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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2014-10-08 15:56:23 UTC

Update Date

2023-02-21 17:30:30 UTC

HMDB ID

HMDB0061875

Secondary Accession Numbers

HMDB61875

Metabolite Identification

Common Name

2-(Dimethylamino)acetonitrile

Description

2-(Dimethylamino)acetonitrile belongs to the class of organic compounds known as trialkylamines. These are organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen. 2-(Dimethylamino)acetonitrile is a very strong basic compound (based on its pKa).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₄H₈N₂

Average Molecular Weight

84.1197

Monoisotopic Molecular Weight

84.068748266

IUPAC Name

2-(dimethylamino)acetonitrile

Traditional Name

acetonitrile, (dimethylamino)

CAS Registry Number

Not Available

SMILES

CN(C)CC#N

InChI Identifier

InChI=1S/C4H8N2/c1-6(2)4-3-5/h4H2,1-2H3

InChI Key

PLXBWEPPAAQASG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trialkylamines. These are organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Trialkylamines

Alternative Parents

Substituents

Alpha-aminonitrile
Tertiary aliphatic amine
Nitrile
Carbonitrile
Organopnictogen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 24421258)

Excreta

Biofluid or Excreta

Feces (PMID: 17314143)

Source

Exogenous

Exogenous (HMDB: HMDB0061875)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	53.8 g/L	ALOGPS
logP	-0.1	ALOGPS
logP	-0.27	ChemAxon
logS	-0.19	ALOGPS
pKa (Strongest Basic)	5.38	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	27.03 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	25.05 m³·mol⁻¹	ChemAxon
Polarizability	9.39 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	116.721	31661259
DarkChem	[M-H]-	110.511	31661259
DeepCCS	[M+H]+	125.578	30932474
DeepCCS	[M-H]-	123.472	30932474
DeepCCS	[M-2H]-	159.458	30932474
DeepCCS	[M+Na]+	133.864	30932474
AllCCS	[M+H]+	121.7	32859911
AllCCS	[M+H-H2O]+	117.3	32859911
AllCCS	[M+NH4]+	125.8	32859911
AllCCS	[M+Na]+	127.0	32859911
AllCCS	[M-H]-	126.6	32859911
AllCCS	[M+Na-2H]-	131.4	32859911
AllCCS	[M+HCOO]-	136.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-(Dimethylamino)acetonitrile	CN(C)CC#N	1158.8	Standard polar	33892256
2-(Dimethylamino)acetonitrile	CN(C)CC#N	703.3	Standard non polar	33892256
2-(Dimethylamino)acetonitrile	CN(C)CC#N	770.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(Dimethylamino)acetonitrile GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-82985fbd0137613b8ad1	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(Dimethylamino)acetonitrile GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Dimethylamino)acetonitrile 10V, Positive-QTOF	splash10-000i-9000000000-347b8a00032cc4b2ce4d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Dimethylamino)acetonitrile 20V, Positive-QTOF	splash10-0006-9000000000-996273ee7cf3cf774389	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Dimethylamino)acetonitrile 40V, Positive-QTOF	splash10-0006-9000000000-b78231b428e4e9d9c94c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Dimethylamino)acetonitrile 10V, Negative-QTOF	splash10-001i-9000000000-18838260eea9b169eaed	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Dimethylamino)acetonitrile 20V, Negative-QTOF	splash10-001i-9000000000-ede7ef8e26816caae8d3	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Dimethylamino)acetonitrile 40V, Negative-QTOF	splash10-0006-9000000000-0a7845f0520861f6776e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Dimethylamino)acetonitrile 10V, Positive-QTOF	splash10-000i-9000000000-d499dd014f8827e63d18	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Dimethylamino)acetonitrile 20V, Positive-QTOF	splash10-0a59-9000000000-5b55da1d266df0255de9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Dimethylamino)acetonitrile 40V, Positive-QTOF	splash10-0006-9000000000-bbf53c8703b87f3ffbab	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Dimethylamino)acetonitrile 10V, Negative-QTOF	splash10-001i-9000000000-40c42ba9e6a3b955ce68	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Dimethylamino)acetonitrile 20V, Negative-QTOF	splash10-001i-9000000000-40c42ba9e6a3b955ce68	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Dimethylamino)acetonitrile 40V, Negative-QTOF	splash10-014i-9000000000-f5af67d69150cf77cf47	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces
Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Clostridium difficile infection	17314143	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61237

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Wu FY, Li Z, Wen ZC, Zhou N, Zhao YF, Jiang YB: A novel thiourea-based dual fluorescent anion receptor with a rigid hydrazine spacer. Org Lett. 2002 Sep 19;4(19):3203-5. [PubMed:12227749 ]
Saczewski F, Bulakowska A, Bednarski P, Grunert R: Synthesis, structure and anticancer activity of novel 2,4-diamino-1,3,5-triazine derivatives. Eur J Med Chem. 2006 Feb;41(2):219-25. Epub 2005 Dec 27. [PubMed:16377034 ]
Van Tassle AJ, Prantil MA, Fleming GR: Investigation of the excited state structure of DCM via ultrafast electronic pump/vibrational probe. J Phys Chem B. 2006 Sep 28;110(38):18989-95. [PubMed:16986894 ]
Bera M, Noll BC: Two new oximate-bridged square-planar dinuclear nickel(II) complexes. Acta Crystallogr C. 2007 Dec;63(Pt 12):m553-6. Epub 2007 Nov 14. [PubMed:18057592 ]
Liu JL, Yan CW, Li YT, Wu ZY, Zhang WJ: Diacetonitrile-1kappaN,3kappaN-bis{mu-trans-N-[3-(dimethylamino)propyl]-N'-(2-hyd roxyethyl)oxamidato(2-)}-1:2kappa(5)N,N',O:O',N'';2:3kappa(5)O',N'':N,N',O-dithio cyanato-1kappaN,3kappaN-tricopper(II). Acta Crystallogr C. 2008 Apr;64(Pt 4):m149-52. doi: 10.1107/S0108270108003296. Epub 2008 Mar 8. [PubMed:18391374 ]
Gavara R, Laia CA, Parola AJ, Pina F: Formation of a leuco spirolactone from 4-(2-carboxyphenyl)-7-diethylamino-4'-dimethylamino-1-benzopyrylium: design of a phase-change thermochromic system based on a flavylium dye. Chemistry. 2010 Jul 12;16(26):7760-6. doi: 10.1002/chem.200903482. [PubMed:20509126 ]
Costero AM, Parra M, Gil S, Gotor R, Mancini PM, Martinez-Manez R, Sancenon F, Royo S: Chromo-fluorogenic detection of nerve-agent mimics using triggered cyclization reactions in push-pull dyes. Chem Asian J. 2010 Jul 5;5(7):1573-85. doi: 10.1002/asia.201000058. [PubMed:20512798 ]
Sahu S, Mishra A, Krishnamoorthy G: Specific site binding of metal ions on the intramolecular charge transfer fluorophore in micelles. Analyst. 2013 Oct 21;138(20):5942-8. doi: 10.1039/c3an00978e. Epub 2013 Aug 9. [PubMed:23936896 ]
Chen H, Sun Y, Zhou C, Cao D, Liu Z, Ma L: Three hydroxy aurone compounds as chemosensors for cyanide anions. Spectrochim Acta A Mol Biomol Spectrosc. 2013 Dec;116:389-93. doi: 10.1016/j.saa.2013.07.041. Epub 2013 Aug 1. [PubMed:23973584 ]
Nobuyuki Ishibe, Jimmie K. Harden, 'Trichloroethylene composition stabilized against oxidation.' U.S. Patent US4404412, issued March, 1977. [Link]

Showing metabocard for 2-(Dimethylamino)acetonitrile (HMDB0061875)

MOL for HMDB0061875 (2-(Dimethylamino)acetonitrile)

3D MOL for HMDB0061875 (2-(Dimethylamino)acetonitrile)

3D SDF for HMDB0061875 (2-(Dimethylamino)acetonitrile)

3D-SDF for HMDB0061875 (2-(Dimethylamino)acetonitrile)

PDB for HMDB0061875 (2-(Dimethylamino)acetonitrile)

3D PDB for HMDB0061875 (2-(Dimethylamino)acetonitrile)

SMILES for HMDB0061875 (2-(Dimethylamino)acetonitrile)

INCHI for HMDB0061875 (2-(Dimethylamino)acetonitrile)

Structure for HMDB0061875 (2-(Dimethylamino)acetonitrile)

3D Structure for HMDB0061875 (2-(Dimethylamino)acetonitrile)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra