NP-MRD: Showing NP-Card for Tetramethylpyrazine (NP0000349)

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Record Information

Version

2.0

Created at

2012-09-11 21:44:31 UTC

Updated at

2025-02-11 15:49:00 UTC

NP-MRD ID

NP0000349

Natural Product DOI

https://doi.org/10.57994/2998

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tetramethylpyrazine

Description

Tetramethylpyrazine, or 2,3,5,6-tetramethylpyrazine, or TMP and also known as FEMA 3237, is an alkylpyrazine and belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms. Tetramethylpyrazine is a moderately basic compound with white crystals that are soluble in alcohol, fixed oils, propylene glycol and water. Its odor is described as nutty, musty and vanilla with dry, brown cocoa nuances and it taste is described as nutty, musty, cocoa, drying, peanut-like with raw coffee notes. Tetramethylpyrazine has been detected in roasted beef, cheddar cheese, dairy products, red and yellow bell peppers (c. Annuum), potato, filberts, boiled egg, coconut endosperm, cocoa products, green tea, tea leaf, soybean products, soybean seed, macadamia nut, peanut, meat, guava fruit, shrimp, rum and whiskey. This could make tetramethylpyrazine a potential biomarker for the consumption of these foods. It has been used as a perfuming agent in soaps, detergents, toiletries, fabric softeners, bleach, alcoholic beverages, and fine fragrances. Its biosynthesis in Bacillus involves the amination of acetoin, the latter being derived from pyruvate (doi:10.1038/1951103A0). It exhibits potential nootropic (improved executive function PMID:23916742 ) And anti-inflammatory activities against induced cerebral ischemic in rats (PMID:23644042 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv1652306242117433D          

 22 22  0  0  0  0            999 V2000
   -2.3655   -1.3891    0.6700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1130   -0.6464    0.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0823   -1.2057    0.5760 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2244   -0.5794    0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5128   -1.2154    0.5756 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1499    0.6557   -0.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3798    1.4208   -0.6988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0433    1.2192   -0.5959 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1660    0.5903   -0.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5244    1.1573   -0.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1081   -2.1547    1.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0966   -0.6691    1.1121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8256   -1.8566   -0.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1314   -0.4774    1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0264   -1.5422   -0.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4009   -2.0855    1.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2331    1.1942   -0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6193    1.1669   -1.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1389    2.4997   -0.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9500    1.6042    0.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2203    0.3678   -0.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4866    1.9455   -1.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9  2  1  0  0  0  0
  1 11  1  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  5 14  1  0  0  0  0
  5 15  1  0  0  0  0
  5 16  1  0  0  0  0
  7 17  1  0  0  0  0
  7 18  1  0  0  0  0
  7 19  1  0  0  0  0
 10 20  1  0  0  0  0
 10 21  1  0  0  0  0
 10 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000349

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])([H])C1=NC(=C(N=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3

> <INCHI_KEY>
FINHMKGKINIASC-UHFFFAOYSA-N

> <FORMULA>
C8H12N2

> <MOLECULAR_WEIGHT>
136.1943

> <EXACT_MASS>
136.100048394

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
16.023429816184183

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
tetramethylpyrazine

> <ALOGPS_LOGP>
1.46

> <JCHEM_LOGP>
0.06338163800000016

> <ALOGPS_LOGS>
-0.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.189242582387245

> <JCHEM_POLAR_SURFACE_AREA>
25.78

> <JCHEM_REFRACTIVITY>
40.1102

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pyrazine, tetramethyl-

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.365  -1.389   0.670  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.113  -0.646   0.308  0.00  0.00           C+0
HETATM    3  N   UNK     0       0.082  -1.206   0.576  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.224  -0.579   0.271  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.513  -1.215   0.576  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.150   0.656  -0.326  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.380   1.421  -0.699  0.00  0.00           C+0
HETATM    8  N   UNK     0      -0.043   1.219  -0.596  0.00  0.00           N+0
HETATM    9  C   UNK     0      -1.166   0.590  -0.290  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.524   1.157  -0.561  0.00  0.00           C+0
HETATM   11  H   UNK     0      -2.108  -2.155   1.426  0.00  0.00           H+0
HETATM   12  H   UNK     0      -3.097  -0.669   1.112  0.00  0.00           H+0
HETATM   13  H   UNK     0      -2.826  -1.857  -0.205  0.00  0.00           H+0
HETATM   14  H   UNK     0       3.131  -0.477   1.131  0.00  0.00           H+0
HETATM   15  H   UNK     0       3.026  -1.542  -0.365  0.00  0.00           H+0
HETATM   16  H   UNK     0       2.401  -2.086   1.253  0.00  0.00           H+0
HETATM   17  H   UNK     0       3.233   1.194  -0.032  0.00  0.00           H+0
HETATM   18  H   UNK     0       2.619   1.167  -1.758  0.00  0.00           H+0
HETATM   19  H   UNK     0       2.139   2.500  -0.603  0.00  0.00           H+0
HETATM   20  H   UNK     0      -2.950   1.604   0.368  0.00  0.00           H+0
HETATM   21  H   UNK     0      -3.220   0.368  -0.926  0.00  0.00           H+0
HETATM   22  H   UNK     0      -2.487   1.946  -1.332  0.00  0.00           H+0
CONECT    1    2   11   12   13                                             
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4   14   15   16                                             
CONECT    6    4    7    8                                                  
CONECT    7    6   17   18   19                                             
CONECT    8    6    9                                                       
CONECT    9    8   10    2                                                  
CONECT   10    9   20   21   22                                             
CONECT   11    1                                                            
CONECT   12    1                                                            
CONECT   13    1                                                            
CONECT   14    5                                                            
CONECT   15    5                                                            
CONECT   16    5                                                            
CONECT   17    7                                                            
CONECT   18    7                                                            
CONECT   19    7                                                            
CONECT   20   10                                                            
CONECT   21   10                                                            
CONECT   22   10                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Value	Source
2,3,5,6,-Tetramethyl-1,4-pyrazine	ChEBI
2,3,5,6-Tetramethylpyrazine	ChEBI
FEMA 3237	ChEBI
FEMA no. 3237	ChEBI
Liqustrazine	ChEBI
TMP	ChEBI
2356-Tetramethyl-pyrazine	HMDB
2356-Tetramethylpyrazine	HMDB
Chuanxiongzine	HMDB
Ligustizine	HMDB
Ligustrazine	HMDB
Tetramethylpyrazin	HMDB
Tetrapyrazine	HMDB
TMP?	HMDB
Tetramethyl pyrazine	HMDB
Tetramethylpyrazine hydrochloride	HMDB
TMPZ	HMDB

Chemical Formula

C₈H₁₂N₂

Average Mass

136.1943 Da

Monoisotopic Mass

136.10005 Da

IUPAC Name

tetramethylpyrazine

Traditional Name

pyrazine, tetramethyl-

CAS Registry Number

1124-11-4

SMILES

[H]C([H])([H])C1=NC(=C(N=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3

InChI Key

FINHMKGKINIASC-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-27	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-27	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-27	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, CDCl₃, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-27	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Camellia sinensis	LOTUS Database	35616633
Capsicum annuum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cocos nucifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Coffea arabica	LOTUS Database	35616633
Coffea arabica L.	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephora	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Corynebacterium glutamicum	LOTUS Database	35616633
Curcuma aromatica	LOTUS Database	35616633
Ephedra sinica	KNApSAcK Database	22123792
Glycine max	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Gossypium hirsutum	LOTUS Database	35616633
Jatropha podagrica	LOTUS Database	35616633
Ligusticum sinense	LOTUS Database	35616633
Panax ginseng	LOTUS Database	35616633
Sergia lucens	LOTUS Database	35616633
Solanum tuberosum	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Theobroma cacao	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrazines

Direct Parent

Pyrazines

Alternative Parents

Substituents

Pyrazine
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	86 °C	Not Available
Boiling Point	190.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	7007 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.28	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	15 g/L	ALOGPS
logP	1.46	ALOGPS
logP	0.063	ChemAxon
logS	-0.96	ALOGPS
pKa (Strongest Basic)	2.19	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	25.78 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	40.11 m³·mol⁻¹	ChemAxon
Polarizability	16.02 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0036584

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015495

KNApSAcK ID

C00056171

Chemspider ID

13658

KEGG Compound ID

Not Available

BioCyc ID

CPD-15901

BiGG ID

Not Available

Wikipedia Link

Tetramethylpyrazine

METLIN ID

Not Available

PubChem Compound

14296

PDB ID

Not Available

ChEBI ID

133246

Good Scents ID

rw1009291

References

General References

Zhu XL, Xiong LZ, Wang Q, Liu ZG, Ma X, Zhu ZH, Hu S, Gong G, Chen SY: Therapeutic time window and mechanism of tetramethylpyrazine on transient focal cerebral ischemia/reperfusion injury in rats. Neurosci Lett. 2009 Jan 2;449(1):24-7. doi: 10.1016/j.neulet.2008.09.007. Epub 2008 Sep 6. [PubMed:18790005 ]
Dai XZ, Bache RJ: Coronary and systemic hemodynamic effects of tetramethylpyrazine in the dog. J Cardiovasc Pharmacol. 1985 Sep-Oct;7(5):841-9. [PubMed:2413290 ]
Li M, Handa S, Ikeda Y, Goto S: Specific inhibiting characteristics of tetramethylpyrazine, one of the active ingredients of the Chinese herbal medicine 'Chuanxiong,' on platelet thrombus formation under high shear rates. Thromb Res. 2001 Oct 1;104(1):15-28. [PubMed:11583735 ]
Wu W, Yu X, Luo XP, Yang SH, Zheng D: Tetramethylpyrazine protects against scopolamine-induced memory impairments in rats by reversing the cAMP/PKA/CREB pathway. Behav Brain Res. 2013 Sep 15;253:212-6. doi: 10.1016/j.bbr.2013.07.052. Epub 2013 Aug 2. [PubMed:23916742 ]
Kao TK, Chang CY, Ou YC, Chen WY, Kuan YH, Pan HC, Liao SL, Li GZ, Chen CJ: Tetramethylpyrazine reduces cellular inflammatory response following permanent focal cerebral ischemia in rats. Exp Neurol. 2013 Sep;247:188-201. doi: 10.1016/j.expneurol.2013.04.010. Epub 2013 Apr 30. [PubMed:23644042 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing NP-Card for Tetramethylpyrazine (NP0000349)

MOL for NP0000349 (Tetramethylpyrazine)

3D MOL for NP0000349 (Tetramethylpyrazine)

3D SDF for NP0000349 (Tetramethylpyrazine)

3D-SDF for NP0000349 (Tetramethylpyrazine)

PDB for NP0000349 (Tetramethylpyrazine)

3D PDB for NP0000349 (Tetramethylpyrazine)

SMILES for NP0000349 (Tetramethylpyrazine)

INCHI for NP0000349 (Tetramethylpyrazine)

Structure for NP0000349 (Tetramethylpyrazine)

3D Structure for NP0000349 (Tetramethylpyrazine)