Methoxamine (CED0005688)

Record Information

Version

1.0

Creation Date

2016-05-25 18:22:30 UTC

Update Date

2026-08-18 12:08:14 UTC

Accession Number

CHEM022167

Identification

Common Name

Methoxamine

Class

Small Molecule

Description

Methoxamine is an organic compound with the formula C11H17NO3 and an average molecular weight of 211.26 g/mol. Methoxamine belongs to the methoxybenzenes, a subclass of benzene and substituted derivatives within the organic compounds. This compound is associated with six recorded sources, including healthcare, pharmaceuticals, and veterinary products specifically as cardiac stimulants excluding cardiac glycosides. It is also found in food preservation, perfumes within detergents and soaps, and electrical and electronic equipment such as television systems, electrically stimulated smoking devices, and conductors or conductive bodies characterised by the conductive materials. Recorded exposure routes for the substance include intravenous and intramuscular administration. At the molecular level, methoxamine acts on three recorded protein targets. It functions as an agonist and binder of the Alpha-1A adrenergic receptor (ADRA1A), the Alpha-1B adrenergic receptor (ADRA1B), and the Alpha-1D adrenergic receptor (ADRA1D).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Methoxamedrine	ChEBI
Methoxamin	ChEBI
Vasoxyl	HMDB
Glaxo wellcome brand 2 OF methoxamine hydrochloride	HMDB
Methoxamine hydrochloride	HMDB
Vasylox	HMDB
Glaxo wellcome brand 1 OF methoxamine hydrochloride	HMDB
Vasoxin	HMDB
Vasoxine	HMDB
Wellcome brand OF methoxamine hydrochloride	HMDB
Hydrochloride, methoxamine	HMDB
Methoxamedrin	HMDB
Metoxamine wellcome	HMDB
Wellcome, metoxamine	HMDB

Chemical Formula

C₁₁H₁₇NO₃

Average Molecular Mass

211.258 g/mol

Monoisotopic Mass

211.121 g/mol

CAS Registry Number

390-28-3

IUPAC Name

2-amino-1-(2,5-dimethoxyphenyl)propan-1-ol

Traditional Name

methoxamine

SMILES

COC1=CC(C(O)C(C)N)=C(OC)C=C1

InChI Identifier

InChI=1S/C11H17NO3/c1-7(12)11(13)9-6-8(14-2)4-5-10(9)15-3/h4-7,11,13H,12H2,1-3H3

InChI Key

WJAJPNHVVFWKKL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Methoxybenzenes

Direct Parent

Dimethoxybenzenes

Alternative Parents

Substituents

Dimethoxybenzene
P-dimethoxybenzene
Phenylpropane
Anisole
Phenol ether
Phenoxy compound
Alkyl aryl ether
Aralkylamine
Secondary alcohol
1,2-aminoalcohol
Ether
Aromatic alcohol
Primary amine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Amine
Organic oxygen compound
Alcohol
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

amphetamines (CHEBI:6839 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	9.21 g/L	ALOGPS
logP	0.41	ALOGPS
logP	0.57	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	13.61	ChemAxon
pKa (Strongest Basic)	9.28	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	64.71 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	57.84 m³·mol⁻¹	ChemAxon
Polarizability	22.81 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum	splash10-014i-0900000000-c18e80e68507135a55de	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-000f-1980000000-5a3cb42851d6378d998c	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-014i-0900000000-c18e80e68507135a55de	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-000f-1980000000-5a3cb42851d6378d998c	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0006-9400000000-f95f18aaa517d345558f	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-000f-9170000000-5a7687b88a5e5736ea53	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03dl-0690000000-5602a5d1ca570bcf9aa6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0900000000-1b92cefe5d27ce45aad1	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03dj-0900000000-bd56a39cbf83b4b15579	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03kj-1900000000-4dc22029f0246da362e5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01bd-4900000000-5bd9da97330739f95161	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0900000000-89ab0b5f7f3887939aea	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0ai0-9800000000-28efb5b4aad0fd8abd82	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-9500000000-6c71c8b0a10f1af4a6f3	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0k97-5900000000-725173a2cbd2a15f8105	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03fu-0900000000-0dc780e113d2bc5b1024	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0900000000-00f066e5e69f13588eec	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-05tf-6900000000-59dd8ab3029dd0ce3690	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-0900000000-188e3234b8e8063962d8	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0596-6900000000-3a39f10dd453930e5977	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03dl-0900000000-9731c275bf5d63e8a01c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01ox-0940000000-d9e757b7d1068e357dec	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004l-0900000000-125668ca28b2b041fda5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-06vi-2900000000-6a7f29f71b196055ca17	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0690000000-1aa8bde9e66ac0010632	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01p6-0920000000-56987f7fa245e6bbb475	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-06ri-2900000000-03625bf389b14ac47819	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-002f-0920000000-70e7df44e0d24606d1a3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ufu-0900000000-fb436c23667d8faf38ca	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000l-7900000000-ee5181b465c5fed70f2e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-1290000000-8c5dbabc0c59be169f69	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0abi-9810000000-2fe8b8454186c8ad8b4d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03dr-2900000000-5fa6c8cc28e31e652a19	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
506.0	Log mg/kg	[280:900]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
10	Insecticides	Agriculture & land management	Not Available
286	Cardiac stimulants excl. cardiac glycosides	Healthcare, pharmaceuticals & veterinary products	Not Available
511	Conductors Or Conductive Bodies Characterised By The Conductive Materials	Electrical & Electronic Equipment	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available
545	Food Preservation	Food, food processing & cookware	Not Available
561	Perfumes Within Detergents And Soaps	Household cleaning & consumer products	Not Available
580	Manufacture Preparation Of Tobacco Products	Industrial manufacturing & chemical processing	Not Available
596	Acaricides	Agriculture & land management	Not Available
600	Herbicides And Algicides	Agriculture & land management	Not Available
602	Molluscicides	Agriculture & land management	Not Available
603	Nematocides	Agriculture & land management	Not Available
605	Pest Repellants	Agriculture & land management	Not Available
606	Plant Growth Regulators	Agriculture & land management	Not Available
610	Aftersun Products	Personal care & cosmetics	Not Available
611	Anti Perspirants Or Body Deoderants	Personal care & cosmetics	Not Available
613	Depilatories	Personal care & cosmetics	Not Available
615	Eye Makeup Products	Personal care & cosmetics	Not Available
617	Lip Care Products	Personal care & cosmetics	Not Available
618	Lip Makeup Products	Personal care & cosmetics	Not Available
632	Apparel	Textiles, leather & furnishings	Not Available

Pathways

2 pathways

Methoxamine Drug Metabolism

Methoxamine Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P30994	Rattus norvegicus	Predicted (SEA)	4.28171
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P08909	Rat	Predicted (SEA)	45.3082
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P14842	Rattus norvegicus	Predicted (SEA)	152.04
Click to view 3D structure	Amine oxidase [flavin-containing] A	P21396	Rattus norvegicus	Predicted (SEA)	20.63
Click to view 3D structure	Alpha-1A adrenergic receptor	P35348	Humans	Predicted (SEA)	171.346
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	306.337
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	180.61
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	439.07
Click to view 3D structure	Alpha-1A adrenergic receptor	P43140	Rattus norvegicus	Predicted (SEA)	133.122
Click to view 3D structure	Prostaglandin G/H synthase 1	P23219	Humans	Predicted (SEA)	55.9736
Click to view 3D structure	Aldo-keto reductase family 1 member C3	P42330	Humans	Predicted (SEA)	36.4334
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	358.262
Click to view 3D structure	Cytochrome P450 1A1	P04798	Humans	Predicted (SEA)	42.4278
Click to view 3D structure	Cytochrome P450 1B1	Q16678	Humans	Predicted (SEA)	53.5603
Click to view 3D structure	Alpha-2B adrenergic receptor	P19328	Rattus norvegicus	Predicted (SEA)	8.17417
Click to view 3D structure	Cytochrome P450 1A2	P05177	Humans	Predicted (SEA)	494.498
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	526.261
Click to view 3D structure	Prostaglandin G/H synthase 2	P35354	Humans	Predicted (SEA)	120.355
Click to view 3D structure	Aldo-keto reductase family 1 member C2	P52895	Humans	Predicted (SEA)	38.6132
Click to view 3D structure	Alpha-1D adrenergic receptor	P23944	Rattus norvegicus	Predicted (SEA)	70.9206
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	370.796
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	314.589
Click to view 3D structure	Trace amine-associated receptor 1	Q96RJ0	Humans	Predicted (SEA)	31.2954
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	508.2
Click to view 3D structure	Dihydrofolate reductase	P00374	Humans	Predicted (SEA)	45.1525