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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:44:41 UTC

Update Date

2023-02-21 17:21:08 UTC

HMDB ID

HMDB0031659

Secondary Accession Numbers

HMDB31659

Metabolite Identification

Common Name

3-Methyl-1-butylamine

Description

3-Methyl-1-butylamine, also known as isoamylamine or 3,3-dimethylpropylamine, belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group. A primary aliphatic amine that is butan-1-amine carrying a methyl substituent at position 3. 3-Methyl-1-butylamine is an ammonia and unpleasant tasting compound. 3-methyl-1-butylamine has been detected, but not quantified, in several different foods, such as green vegetables, black elderberries, root vegetables, corns, and french plantains. This could make 3-methyl-1-butylamine a potential biomarker for the consumption of these foods.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Amino-3-methylbutane	ChEBI
3,3-Dimethylpropylamine	ChEBI
3-Methylbutanamine	ChEBI
gamma-Isoamylamine	ChEBI
Isoamylamine	ChEBI
Isobutylcarbylamine	ChEBI
Isovalerylamine	ChEBI
Leucamine	ChEBI
Isopentylamine	Kegg
g-Isoamylamine	Generator
Γ-isoamylamine	Generator
1-Aminoisopentane	HMDB
3,3-Dimethyl-propylamine	HMDB
3-Methyl-1-butanamine	HMDB
3-Methyl-1-butanamine, 9ci	HMDB
3-Methyl-butylamine	HMDB
3-METHYLBUTAN-1-amine	HMDB
3-Methylbutylamine	HMDB, MeSH
FEMA 3219	HMDB
Isoamylamine, reag	HMDB
laquo gammaraquo -Isoamylamine	HMDB
LEN	HMDB
Monoisoamylamine	HMDB
Monoisopentylamine	HMDB
Isoamylamine hydrochloride	MeSH, HMDB
Isoamylamine carbonate (1:1)	MeSH, HMDB

Chemical Formula

C₅H₁₃N

Average Molecular Weight

87.1634

Monoisotopic Molecular Weight

87.104799421

IUPAC Name

3-methylbutan-1-amine

Traditional Name

isoamylamine

CAS Registry Number

107-85-7

SMILES

CC(C)CCN

InChI Identifier

InChI=1S/C5H13N/c1-5(2)3-4-6/h5H,3-4,6H2,1-2H3

InChI Key

BMFVGAAISNGQNM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Monoalkylamines

Alternative Parents

Substituents

Organopnictogen compound
Hydrocarbon derivative
Primary aliphatic amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

primary aliphatic amine (CHEBI:43689 )

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0031659)
Cytoplasm (HMDB: HMDB0031659)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031659)

Source

Endogenous

Endogenous (HMDB: HMDB0031659)

Plant

Plant (HMDB: HMDB0031659)
Poaceae (HMDB: HMDB0031659)

Animal

Animal (HMDB: HMDB0031659)

Exogenous

Food

Food (HMDB: HMDB0031659)

Beverage

Fermented beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereal

Corn (FooDB: FOOD00205)

Cereals and cereal products (FooDB: FOOD00858)

Vegetable

Mushroom

Leaf vegetable

Spinach (FooDB: FOOD00178)
Green vegetables (FooDB: FOOD00872)

Root vegetable

Root vegetables (FooDB: FOOD00873)

Fruit

Tropical fruit

French plantain (FooDB: FOOD00436)

Berry

Common grape (FooDB: FOOD00204)
Black elderberry (FooDB: FOOD00166)

Pome

Pomes (FooDB: FOOD00856)

Fruits (FooDB: FOOD00871)

Milk and milk product

Milk and milk products (FooDB: FOOD00863)

Exogenous (HMDB: HMDB0031659)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-60.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	95.00 to 97.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	109700 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.410 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	16.1 g/L	ALOGPS
logP	1.15	ALOGPS
logP	0.99	ChemAxon
logS	-0.73	ALOGPS
pKa (Strongest Basic)	10.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.02 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	28.34 m³·mol⁻¹	ChemAxon
Polarizability	11.48 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]+	116.656	31661259
DarkChem	[M-H]-	111.338	31661259
DeepCCS	[M+H]+	125.13	30932474
DeepCCS	[M-H]-	122.559	30932474
DeepCCS	[M-2H]-	158.681	30932474
DeepCCS	[M+Na]+	133.667	30932474
AllCCS	[M+H]+	122.2	32859911
AllCCS	[M+H-H2O]+	117.8	32859911
AllCCS	[M+NH4]+	126.3	32859911
AllCCS	[M+Na]+	127.5	32859911
AllCCS	[M-H]-	131.6	32859911
AllCCS	[M+Na-2H]-	136.4	32859911
AllCCS	[M+HCOO]-	141.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.48 minutes	32390414
Predicted by Siyang on May 30, 2022	9.6659 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.59 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	184.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	748.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	338.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	107.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	207.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	66.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	311.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	305.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	408.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	674.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	231.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	824.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	212.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	254.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	514.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	407.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	114.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-1-butylamine	CC(C)CCN	1021.0	Standard polar	33892256
3-Methyl-1-butylamine	CC(C)CCN	672.8	Standard non polar	33892256
3-Methyl-1-butylamine	CC(C)CCN	699.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-1-butylamine,1TMS,isomer #1	CC(C)CCN[Si](C)(C)C	931.0	Semi standard non polar	33892256
3-Methyl-1-butylamine,1TMS,isomer #1	CC(C)CCN[Si](C)(C)C	937.4	Standard non polar	33892256
3-Methyl-1-butylamine,2TMS,isomer #1	CC(C)CCN([Si](C)(C)C)[Si](C)(C)C	1198.2	Semi standard non polar	33892256
3-Methyl-1-butylamine,2TMS,isomer #1	CC(C)CCN([Si](C)(C)C)[Si](C)(C)C	1190.3	Standard non polar	33892256
3-Methyl-1-butylamine,1TBDMS,isomer #1	CC(C)CCN[Si](C)(C)C(C)(C)C	1158.3	Semi standard non polar	33892256
3-Methyl-1-butylamine,1TBDMS,isomer #1	CC(C)CCN[Si](C)(C)C(C)(C)C	1135.9	Standard non polar	33892256
3-Methyl-1-butylamine,2TBDMS,isomer #1	CC(C)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1553.7	Semi standard non polar	33892256
3-Methyl-1-butylamine,2TBDMS,isomer #1	CC(C)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1580.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3-Methyl-1-butylamine EI-B (Non-derivatized)	splash10-001i-9000000000-a38f41cef45a48b3b69d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Methyl-1-butylamine EI-B (Non-derivatized)	splash10-001i-9000000000-a38f41cef45a48b3b69d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-1-butylamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9000000000-250861c17f6653736aa3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-1-butylamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-6bbe2b2e1994246ba25c	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methyl-1-butylamine LC-ESI-QQ , positive-QTOF	splash10-000i-9000000000-469a52d1e9797b41e3be	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methyl-1-butylamine LC-ESI-QQ , positive-QTOF	splash10-006x-9000000000-fc2643a5767684b8bc95	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methyl-1-butylamine LC-ESI-QQ , positive-QTOF	splash10-0006-9000000000-000e48c943499c169bdd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methyl-1-butylamine LC-ESI-QQ , positive-QTOF	splash10-0006-9000000000-ccfecc37aae2b909c394	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methyl-1-butylamine LC-ESI-QQ , positive-QTOF	splash10-000f-9000000000-6ce1c7de6adde7b9b85c	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1-butylamine 10V, Positive-QTOF	splash10-0079-9000000000-7fc3dae42e58a875d315	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1-butylamine 20V, Positive-QTOF	splash10-00di-9000000000-dbc7a46550f8a1ee57bf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1-butylamine 40V, Positive-QTOF	splash10-0ab9-9000000000-262c4fd7c95dcc6eaf8f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1-butylamine 10V, Negative-QTOF	splash10-000i-9000000000-f7528eebb5e541382ef9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1-butylamine 20V, Negative-QTOF	splash10-000i-9000000000-2dc7fbcba7e740af6082	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1-butylamine 40V, Negative-QTOF	splash10-066r-9000000000-08df561ff8b1d510b437	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1-butylamine 10V, Negative-QTOF	splash10-001r-9000000000-02b05e2623e9036ba029	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1-butylamine 20V, Negative-QTOF	splash10-001r-9000000000-a7a1e628a927737990e7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1-butylamine 40V, Negative-QTOF	splash10-00du-9000000000-f0dbf3f43767c4a4ac17	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1-butylamine 10V, Positive-QTOF	splash10-0079-9000000000-3f085e3bda443c51cc9f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1-butylamine 20V, Positive-QTOF	splash10-05fr-9000000000-b743c332bb84f5864106	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1-butylamine 40V, Positive-QTOF	splash10-0006-9000000000-5002c7b10e36c65cc5bd	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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+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

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7894

PDB ID

Not Available

ChEBI ID

43689

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1035551

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 3-Methyl-1-butylamine (HMDB0031659)

MOL for HMDB0031659 (3-Methyl-1-butylamine)

3D MOL for HMDB0031659 (3-Methyl-1-butylamine)

3D SDF for HMDB0031659 (3-Methyl-1-butylamine)

3D-SDF for HMDB0031659 (3-Methyl-1-butylamine)

PDB for HMDB0031659 (3-Methyl-1-butylamine)

3D PDB for HMDB0031659 (3-Methyl-1-butylamine)

SMILES for HMDB0031659 (3-Methyl-1-butylamine)

INCHI for HMDB0031659 (3-Methyl-1-butylamine)

Structure for HMDB0031659 (3-Methyl-1-butylamine)

3D Structure for HMDB0031659 (3-Methyl-1-butylamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra