NP-MRD: Showing NP-Card for levomethadyl acetate (NP0319036)

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Record Information

Version

2.0

Created at

2022-09-11 19:52:00 UTC

Updated at

2022-09-11 19:52:00 UTC

NP-MRD ID

NP0319036

Secondary Accession Numbers

None

Natural Product Identification

Common Name

levomethadyl acetate

Description

Levomethadyl Acetate, also known as LAAM or levacetylmethadolum, belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. It also acts as a potent, noncompetitive α3β4 neuronal nicotinic acetylcholine receptor antagonist. Unlike methadone, which requires daily administration, LAAM is administered two to three times a week. Levomethadyl Acetate is a drug which is used for the treatment and management of opiate dependence. It is sometimes used to treat severe pain in terminal patients. It has a melting point of 215 °C and a molecular weight of 353.50. Levomethadyl Acetate is a very strong basic compound (based on its pKa). Levomethadyl acetate can be converted into nor-levomethadyl acetate and formaldehyde through its interaction with the enzyme cytochrome P450 3A7. In humans, levomethadyl acetate is involved in levomethadyl acetate metabolism pathway. In 2001, LAAM was removed from the European market due to reports of life-threatening ventricular rhythm disorders. Levomethadyl Acetate is a potentially toxic compound. levomethadyl acetate is found in Apis cerana. levomethadyl acetate was first documented in 2000 (PMID: 11058673). LAAM is indicated as a second-line treatment for the treatment and management of opioid dependence if patients fail to respond to drugs like methadone or buprenorphine (PMID: 12220607) (PMID: 12646332) (PMID: 15104241) (PMID: 12676878).

Structure

MOL 3D MOL SDF PDB SMILES InChI

1227
  Mrv0541 02231215202D          

 26 27  0  0  1  0            999 V2000
    5.8950   -0.7144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1325    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4253   -0.2482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6575    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8325    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4825    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0572    0.2822    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6575    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6575   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8950    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9140    1.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9430    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9430   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7200    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5685   -1.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9430    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9430   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7200   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6575    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6575   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1325   -1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  6  0  0  0
  1 23  1  0  0  0  0
  2 23  2  0  0  0  0
  7  3  1  1  0  0  0
  3 17  1  0  0  0  0
  3 18  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5  7  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  8 12  2  0  0  0  0
  8 14  1  0  0  0  0
  9 13  2  0  0  0  0
  9 15  1  0  0  0  0
 10 16  1  0  0  0  0
 12 19  1  0  0  0  0
 13 20  1  0  0  0  0
 14 21  2  0  0  0  0
 15 22  2  0  0  0  0
 19 24  2  0  0  0  0
 20 25  2  0  0  0  0
 21 24  1  0  0  0  0
 22 25  1  0  0  0  0
 23 26  1  0  0  0  0
M  END

     RDKit          3D

 57 58  0  0  0  0  0  0  0  0999 V2000
   -1.9217   -1.9058   -2.8722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8149   -1.0240   -2.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1165   -1.0309   -0.7654 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4115   -0.4923   -0.6468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5371   -1.1951   -0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8789   -0.5538   -0.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4307   -2.4135   -0.0231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1138   -0.1926    0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352   -0.7473   -0.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4028   -0.2031    0.5039 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7643    1.2074    0.2298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6008   -1.0083    0.1876 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7624   -0.4865    0.8281 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7250   -1.2696   -1.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3706    1.1797   -0.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3566    1.9196    0.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7093    3.1904   -0.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0327    3.7275   -1.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0408    2.9838   -1.9947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2998    1.7203   -1.5652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4369   -0.2615    1.4618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1924    0.7984    2.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4475    0.7678    3.6796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9811   -0.3803    4.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2371   -1.4500    3.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9712   -1.4052    2.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6114   -2.0311   -3.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0132   -2.8564   -2.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8544   -1.2987   -2.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9119   -0.0559   -2.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1202   -1.5149   -2.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0838   -2.0825   -0.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0695   -0.1355    0.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6383   -1.3276   -0.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9180    0.2948   -0.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1560   -1.8473    0.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4977   -0.8390   -1.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464   -0.3345    1.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0541    1.9585    0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7332    1.4923    0.7550 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0528    1.3617   -0.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5215   -0.0657    1.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3017    0.2825    0.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4908   -1.3426    0.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7844   -1.5263   -1.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0524   -2.1194   -1.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3946   -0.3926   -1.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9518    1.5467    0.9546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4830    3.7824    0.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2875    4.7216   -1.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4958    3.4139   -2.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0732    1.1363   -2.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2154    1.7103    1.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2330    1.6273    4.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1872   -0.4134    5.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6542   -2.3365    3.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1823   -2.2832    1.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  3  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
  8 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  8 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 20 15  1  0
 26 21  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  1
  6 33  1  0
  6 34  1  0
  6 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  1
 11 39  1  0
 11 40  1  0
 11 41  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 14 47  1  0
 16 48  1  0
 17 49  1  0
 18 50  1  0
 19 51  1  0
 20 52  1  0
 22 53  1  0
 23 54  1  0
 24 55  1  0
 25 56  1  0
 26 57  1  0
M  END

1227
  Mrv0541 02231215202D          

 26 27  0  0  1  0            999 V2000
    5.8950   -0.7144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1325    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4253   -0.2482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6575    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8325    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4825    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0572    0.2822    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6575    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6575   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8950    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9140    1.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9430    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9430   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7200    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5685   -1.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9430    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9430   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7200   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6575    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6575   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1325   -1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  6  0  0  0
  1 23  1  0  0  0  0
  2 23  2  0  0  0  0
  7  3  1  1  0  0  0
  3 17  1  0  0  0  0
  3 18  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5  7  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  8 12  2  0  0  0  0
  8 14  1  0  0  0  0
  9 13  2  0  0  0  0
  9 15  1  0  0  0  0
 10 16  1  0  0  0  0
 12 19  1  0  0  0  0
 13 20  1  0  0  0  0
 14 21  2  0  0  0  0
 15 22  2  0  0  0  0
 19 24  2  0  0  0  0
 20 25  2  0  0  0  0
 21 24  1  0  0  0  0
 22 25  1  0  0  0  0
 23 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0319036

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](OC(C)=O)C(C[C@H](C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H31NO2/c1-6-22(26-19(3)25)23(17-18(2)24(4)5,20-13-9-7-10-14-20)21-15-11-8-12-16-21/h7-16,18,22H,6,17H2,1-5H3/t18-,22-/m0/s1

> <INCHI_KEY>
XBMIVRRWGCYBTQ-AVRDEDQJSA-N

> <FORMULA>
C23H31NO2

> <MOLECULAR_WEIGHT>
353.4977

> <EXACT_MASS>
353.235479241

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
40.5322514105547

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,6S)-6-(dimethylamino)-4,4-diphenylheptan-3-yl acetate

> <ALOGPS_LOGP>
4.78

> <JCHEM_LOGP>
4.884769339999999

> <ALOGPS_LOGS>
-5.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.869489670661055

> <JCHEM_POLAR_SURFACE_AREA>
29.54

> <JCHEM_REFRACTIVITY>
117.85760000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.79e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
levomethadyl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1227                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      11.004  -1.334   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      13.314   0.000   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       4.527  -0.463   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       8.694   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.154   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.234   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.707   0.527   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.694   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.694  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.004   1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.439   2.043   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.360   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.028  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.028   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.360  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.544   1.334   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.080   0.064   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.795  -1.980   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.360   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.028  -3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.028   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.360  -3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.544  -1.334   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.694   4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.694  -4.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.314  -2.667   0.000  0.00  0.00           C+0
CONECT    1    6   23                                                       
CONECT    2   23                                                            
CONECT    3    7   17   18                                                  
CONECT    4    5    6    8    9                                             
CONECT    5    4    7                                                       
CONECT    6    1    4   10                                                  
CONECT    7    3    5   11                                                  
CONECT    8    4   12   14                                                  
CONECT    9    4   13   15                                                  
CONECT   10    6   16                                                       
CONECT   11    7                                                            
CONECT   12    8   19                                                       
CONECT   13    9   20                                                       
CONECT   14    8   21                                                       
CONECT   15    9   22                                                       
CONECT   16   10                                                            
CONECT   17    3                                                            
CONECT   18    3                                                            
CONECT   19   12   24                                                       
CONECT   20   13   25                                                       
CONECT   21   14   24                                                       
CONECT   22   15   25                                                       
CONECT   23    1    2   26                                                  
CONECT   24   19   21                                                       
CONECT   25   20   22                                                       
CONECT   26   23                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Value	Source
(-)-alpha-Acetylmethadol	ChEBI
(1S,4S)-4-(Dimethylamino)-1-ethyl-2,2-diphenylpentyl acetate	ChEBI
1-alpha-Acetylmethadol	ChEBI
LAAM	ChEBI
Levacetilmetadol	ChEBI
Levacetylmethadolum	ChEBI
Levomethadyl	ChEBI
Orlaam	ChEBI
Levacetylmethadol	Kegg
(-)-a-Acetylmethadol	Generator
(-)-Α-acetylmethadol	Generator
(1S,4S)-4-(Dimethylamino)-1-ethyl-2,2-diphenylpentyl acetic acid	Generator
1-a-Acetylmethadol	Generator
1-Α-acetylmethadol	Generator
Levomethadyl acetic acid	Generator
Levo-alphacetylmethadol	HMDB
Levo-methadyl acetate	HMDB
Nor-laam	HMDB
Levo-alpha-acetylmethadol	HMDB
Levomethadyl acetate hydrochloride	HMDB
(3R,6R)-3-Acetoxy-6-dimethylamino-4,4-diphenylheptane	HMDB
Dimepheptanol	HMDB
6-(Dimethylamino)-4,4-diphenyl-3-heptanol acetate	HMDB
Alphacetylmethadol	HMDB
Levoacetylmethadol	HMDB
Methadol	HMDB
Acetylmethadol	HMDB
Amidolacetate	HMDB
Acemethadone	HMDB
Levo alpha acetylmethadol	HMDB
Methadyl acetate	HMDB

Chemical Formula

C₂₃H₃₁NO₂

Average Mass

353.4977 Da

Monoisotopic Mass

353.23548 Da

IUPAC Name

(3S,6S)-6-(dimethylamino)-4,4-diphenylheptan-3-yl acetate

Traditional Name

levomethadyl acetate

CAS Registry Number

Not Available

SMILES

CC[C@H](OC(C)=O)C(C[C@H](C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C23H31NO2/c1-6-22(26-19(3)25)23(17-18(2)24(4)5,20-13-9-7-10-14-20)21-15-11-8-12-16-21/h7-16,18,22H,6,17H2,1-5H3/t18-,22-/m0/s1

InChI Key

XBMIVRRWGCYBTQ-AVRDEDQJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Aralkylamine
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary amino compound (CHEBI:6441 )
acetate ester (CHEBI:6441 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.78	ALOGPS
logP	4.88	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Basic)	9.87	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.54 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	117.86 m³·mol⁻¹	ChemAxon
Polarizability	40.53 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0015358

DrugBank ID

DB01227

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

14401

KEGG Compound ID

C08012

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Levomethadyl_Acetate

METLIN ID

Not Available

PubChem Compound

15130

PDB ID

Not Available

ChEBI ID

6441

Good Scents ID

Not Available

References

General References

Johnson RE, Chutuape MA, Strain EC, Walsh SL, Stitzer ML, Bigelow GE: A comparison of levomethadyl acetate, buprenorphine, and methadone for opioid dependence. N Engl J Med. 2000 Nov 2;343(18):1290-7. doi: 10.1056/NEJM200011023431802. [PubMed:11058673 ]
Kreek MJ, Vocci FJ: History and current status of opioid maintenance treatments: blending conference session. J Subst Abuse Treat. 2002 Sep;23(2):93-105. doi: 10.1016/s0740-5472(02)00259-3. [PubMed:12220607 ]
Kuo I, Brady J, Butler C, Schwartz R, Brooner R, Vlahov D, Strathdee SA: Feasibility of referring drug users from a needle exchange program into an addiction treatment program: experience with a mobile treatment van and LAAM maintenance. J Subst Abuse Treat. 2003 Jan;24(1):67-74. doi: 10.1016/s0740-5472(02)00343-4. [PubMed:12646332 ]
Deshmukh SV, Nanovskaya TN, Hankins GD, Ahmed MS: N-demethylation of levo-alpha-acetylmethadol by human placental aromatase. Biochem Pharmacol. 2004 Mar 1;67(5):885-92. doi: 10.1016/j.bcp.2003.10.007. [PubMed:15104241 ]
Nanovskaya TN, Deshmukh SV, Miles R, Burmaster S, Ahmed MS: Transfer of L-alpha-acetylmethadol (LAAM) and L-alpha-acetyl-N-normethadol (norLAAM) by the perfused human placental lobule. J Pharmacol Exp Ther. 2003 Jul;306(1):205-12. doi: 10.1124/jpet.103.050690. Epub 2003 Apr 3. [PubMed:12676878 ]
LOTUS database [Link]

Showing NP-Card for levomethadyl acetate (NP0319036)

MOL for NP0319036 (levomethadyl acetate)

3D MOL for NP0319036 (levomethadyl acetate)

3D SDF for NP0319036 (levomethadyl acetate)

3D-SDF for NP0319036 (levomethadyl acetate)

PDB for NP0319036 (levomethadyl acetate)

3D PDB for NP0319036 (levomethadyl acetate)

SMILES for NP0319036 (levomethadyl acetate)

INCHI for NP0319036 (levomethadyl acetate)

Structure for NP0319036 (levomethadyl acetate)

3D Structure for NP0319036 (levomethadyl acetate)