Cannabis Compound Database: Showing Compound Card for Dimethylamine (CDB006162)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (4) Show 5 proteins XML

Record Information

Version

1.0

Created at

2020-03-18 23:22:09 UTC

Updated at

2021-01-04 20:37:47 UTC

CannabisDB ID

CDB006162

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Dimethylamine

Description

Dimethylamine, DMA, also known as (CH3)2NH, an organic secondary amine, belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. Dimethylamine is strong basic compound that has low toxicity. The DMA ammonium salt (CH3-NH2+-CH3) has a pKa of 10.73 which is higher than the pKa of methylamine (10.64) and trimethylamine (9.79). It is a colorless, liquefied and flammable gas with an ammonia and fish-like odor. It can also be found in solutions of up to 40% DMA in water. Dimethylamine is abundant in human urine, particularly after the consumption of fish and seafoods. The highest concentrations were obtained from individuals that consumed coley, squid and whiting with cod, haddock, sardine, skate and swordfish (PMID: 18282650 ). The main sources of urinary DMA include trimethylamine N-oxide, a common food component, and asymmetric dimethylarginine (ADMA), an endogenous inhibitor of nitric oxide (NO) synthesis. ADMA is excreted in the urine in part unmetabolized and in part after hydrolysis to DMA by dimethylarginine dimethylaminohydrolase (DDAH). In the body, DMA also undergoes nitrosation under weak acid conditions to give dimethlynitrosamine. DMA is an aminating agent in the manufacturing of ion-exchange resins that are used in food processing. DMA is a dehairing agent used in the in tanning process, in dyes, in rubber accelerators, in soaps and cleaning compounds and as an agricultural fungicide. Dimethylamine is produced by the catalytic reaction of methanol and ammonia at elevated temperatures and high pressure. Dimethylamine is a precursor to several industrially significant compounds. It reacts with carbon disulfide to give dimethyldithiocarbamate, a precursor to a family of chemicals widely used in the vulcanization of rubber. The solvents dimethylformamide and dimethylacetamide are derived from dimethylamine. It is a raw material used in the production of many agrichemicals and pharmaceuticals, such as dimefox and diphenhydramine, respectively. The chemical weapon tabun is derived from dimethylamine. The surfactant lauryl dimethylamine oxide is found in soaps and cleaning compounds. Unsymmetrical dimethylhydrazine, a rocket fuel, is prepared from dimethylamine. Dimethylamine reacts with acids to form salts, such as dimethylamine hydrochloride, an odorless white solid with a melting point of 171.5 ¬∞C. It is an attractant for boll weevils. Dimethylamine is also a constituent of cannabis smoke. It is volatilized during the combustion of cannabis ( Ref:DOI ).

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
DMA	ChEBI
HNMe2	ChEBI
Me2nh	ChEBI
N,N-Dimethylamine	ChEBI
(CH3)2nh	Kegg
Dimethylamine anhydrous	HMDB
Dimethylamine anhydrous (dot)	HMDB
Dimethylamine aqueous solution	HMDB
Dimethylamine hydrobromide	HMDB
Dimethylamine solution	HMDB
N-Methyl-methanamine	HMDB
N-Methylmethanamine	HMDB
N-Methylmethanamine (acd/name 4.0)	HMDB
Dimethylamine nitrate	HMDB
Dimethylamine perchlorate	HMDB
Dimethylamine sulfate	HMDB
Dimethylamine hydrochloride	HMDB
Dimethylamine phosphate (3:1)	HMDB
Dimethylamine, conjugate acid	HMDB
Dimethylammonium chloride	HMDB
Dimethylamine sulfate (1:1)	HMDB
Dimethylammonium formate	HMDB
Dimethylamine monosulfate	HMDB

Chemical Formula

C₂H₇N

Average Molecular Weight

45.08

Monoisotopic Molecular Weight

45.0578

IUPAC Name

dimethylamine

Traditional Name

dimethylamine

CAS Registry Number

124-40-3

SMILES

CNC

InChI Identifier

InChI=1S/C2H7N/c1-3-2/h3H,1-2H3

InChI Key

ROSDSFDQCJNGOL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Dialkylamines

Alternative Parents

Substituents

Secondary aliphatic amine
Organopnictogen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

methylamines (CHEBI:17170 )
secondary aliphatic amine (CHEBI:17170 )

Ontology

Dermal

Enteral:

Ingestion

Source:

Biological:

Microbe:

Micrococcus

Arthrobacter:

Arthrobacter globiformis

Biofluid and excreta:

Subcellular:

Role

Indirect biological role:

Uremic toxin

Industrial application:

Food and nutrition

Environmental role:

Air pollutant

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	-92.2 °C	Not Available
Boiling Point	7 - 9 °C	Wikipedia
Water Solubility	1630 mg/mL at 40 °C	Not Available
logP	-0.38	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	-0.53	ALOGPS
logP	-0.19	ChemAxon
logS	1.06	ALOGPS
pKa (Strongest Basic)	10.52	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	12.03 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	14.69 m³·mol⁻¹	ChemAxon
Polarizability	5.75 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-8ae4e0d1cb5c91c730c0	2014-09-20	View Spectrum
GC-MS	Dimethylamine, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-cfb8e10b3b28eba99793	Spectrum
GC-MS	Dimethylamine, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-cfb8e10b3b28eba99793	Spectrum
Predicted GC-MS	Dimethylamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-9000000000-398c710ba4ea34342a91	Spectrum
Predicted GC-MS	Dimethylamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dimethylamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0006-9000000000-8b085007dc085a460422	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0002-9000000000-103f1d373ec0d015b807	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0002-9000000000-df28f146170e28bfcb5e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0002-9000000000-cd82fdde4d83a74d83f1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-00wc-9100000000-aeb1521c62f5010e11aa	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-017i-9101000000-c269a0887eed5daf0e28	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-9000000000-103f1d373ec0d015b807	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-9000000000-df28f146170e28bfcb5e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-9000000000-17646ed4f7c44ba14045	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00wc-9100000000-aeb1521c62f5010e11aa	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-017i-9101000000-c269a0887eed5daf0e28	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-933c4b104db02265ac4a	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-e85cf853d2e7110d18c1	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014j-9000000000-2032c41c4ca525ff4e1c	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-32c57cc32d61a2feae23	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-36fe99d2cc96e560f509	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-8914e111239eacc36328	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-46fb6b0f3d2dcd71d159	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-46fb6b0f3d2dcd71d159	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-46fb6b0f3d2dcd71d159	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-e97e92727205304cdb09	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-e97e92727205304cdb09	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-9cf36baccac69593c69f	2021-09-23	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Citalopram Action Pathway		Not Available
Citalopram Metabolism Pathway		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Amine oxidase [flavin-containing] B	MAOB	Xp11.23	P27338	details
Amine oxidase [flavin-containing] A	MAOA	Xp11.3	P21397	details
N(G),N(G)-dimethylarginine dimethylaminohydrolase 1	DDAH1	1p22	O94760	details
N(G),N(G)-dimethylarginine dimethylaminohydrolase 2	DDAH2	6p21.3	O95865	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
N(G),N(G)-dimethylarginine dimethylaminohydrolase 1	DDAH1	1p22	O94760	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000087

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012589

KNApSAcK ID

Not Available

Chemspider ID

654

KEGG Compound ID

C00543

BioCyc ID

DIMETHYLAMINE

BiGG ID

Not Available

Wikipedia Link

Dimethylamine

METLIN ID

3758

PubChem Compound

674

PDB ID

Not Available

ChEBI ID

17170

References

General References

Mitchell SC, Zhang AQ, Smith RL: Dimethylamine and diet. Food Chem Toxicol. 2008 May;46(5):1734-8. doi: 10.1016/j.fct.2008.01.010. Epub 2008 Jan 15. [PubMed:18282650 ]
Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Meskys R, Harris RJ, Casaite V, Basran J, Scrutton NS: Organization of the genes involved in dimethylglycine and sarcosine degradation in Arthrobacter spp.: implications for glycine betaine catabolism. Eur J Biochem. 2001 Jun;268(12):3390-8. doi: 10.1046/j.1432-1327.2001.02239.x. [PubMed:11422368 ]

Enzymes

Enzyme Details

1. Amine oxidase [flavin-containing] B

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:: MAOB
Uniprot ID:: P27338
Molecular weight:: 58762.475

Enzyme Details

2. Amine oxidase [flavin-containing] A

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
Molecular weight:: 59681.27

Enzyme Details

3. N(G),N(G)-dimethylarginine dimethylaminohydrolase 1

General function:: Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amidines
Specific function:: Hydrolyzes N(G),N(G)-dimethyl-L-arginine (ADMA) and N(G)-monomethyl-L-arginine (MMA) which act as inhibitors of NOS. Has therefore a role in the regulation of nitric oxide generation.
Gene Name:: DDAH1
Uniprot ID:: O94760
Molecular weight:: 20189.135

Enzyme Details

4. N(G),N(G)-dimethylarginine dimethylaminohydrolase 2

General function:: Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amidines
Specific function:: Hydrolyzes N(G),N(G)-dimethyl-L-arginine (ADMA) and N(G)-monomethyl-L-arginine (MMA) which act as inhibitors of NOS. Has therefore a role in the regulation of nitric oxide generation.
Gene Name:: DDAH2
Uniprot ID:: O95865
Molecular weight:: 29643.54

Showing Compound Card for Dimethylamine (CDB006162)

Structure for CDB006162 (Dimethylamine)

Enzymes