CAS 608-07-1 5-Methoxytryptamine (HCID 1833)

Overview

5-methoxytryptamine is a member of the class of tryptamines that is the methyl ether derivative of serotonin. It has a role as a 5-hydroxytryptamine 2B receptor agonist, a 5-hydroxytryptamine 2C receptor agonist, a 5-hydroxytryptamine 2A receptor agonist, an antioxidant, a serotonergic agonist, a neuroprotective agent, a radiation protective agent, a mouse metabolite, a cardioprotective agent and a human metabolite. It is a member of tryptamines, an aromatic ether and a primary amino compound. It is functionally related to a serotonin. It is a conjugate base of a 5-methoxytryptamine(1+).

Names & identifiers

Preferred name: 5-Methoxytryptamine
IUPAC: 2-(5-methoxy-1H-indol-3-yl)ethanamine
English name: 5-Methoxytryptamine
Molecular formula: C11H14N2O
Molecular weight: 190.24

Names & synonyms

5-METHOXYTRYPTAMINE608-07-12-(5-Methoxy-1H-indol-3-yl)ethanamineMethoxytryptamineO-Methylserotonin3-(2-Aminoethyl)-5-methoxyindole5MOT1H-Indole-3-ethanamine, 5-methoxy-5-Mot2-(5-Methoxy-1H-Indol-3-Yl)Ethan-1-Amine5-MeOT5-methoxy-1H-indole-3-ethanamine

Show more names

5-Methoxyindoleacetate2-(5-methoxy-1H-indol-3-yl)acetic acidMEXAMINEMelatonin Related CoMpound AMEXAMINE HYDROCHLORIDE5-METHOXYTRYPTAMINE HCL5-methoxy-1h-indole-3-ethanamin

3VMW6141KCDTXSID60209638NSC-56422CHEBI:20895 MethoxytryptamineMeksamineRefChem:103077DTXCID10132129

Database identifiers

CAS: 608-07-1
PubChem CID: 1833
DTXSID: DTXSID60209638
ChEMBL: CHEMBL8165
ChEBI: CHEBI:2089
UNII: 3VMW6141KC
EC Number: 210-153-7
Nikkaji: J7.009B

Properties

Computed structural properties

XLogP: 0.5
Topological polar surface area: 51 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 2
Rotatable bonds: 3
Heavy atoms: 14
Formal charge: 0
Complexity: 186

Experimental & physicochemical properties

Melting Point121.5 °C

Physical DescriptionSolid

Collision Cross Section · 3 items

143.3 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

142.7 Å² [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

141.18 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

Physicochemical properties

Melting point: 121 · 121-123 °C (lit.)
Boiling point: 325.75 °C · 325.75°C (rough estimate)
Density: 1.0815 · 1.0815 (rough estimate)
refractive index: 1.57 · 1.5700 (estimate)
storage temp.: 2 · 2-8°C
solubility: Chloroform (Slightly), Methanol (Slightly)
form: crystalline
pka: 16.91 · 16.91±0.30(Predicted)
color: white
Merck: 13 · 13,6032
BRN: 145587 · 145587
InChI: InChI=1S/C11H14N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3
InChIKey: JTEJPPKMYBDEMY-UHFFFAOYSA-N
SMILES: N1C2=C(C=C(OC)C=C2)C(CCN)=C1
CAS DataBase Reference: 608 · 608-07-1(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 3 VMW6141KC · 3VMW6141KC
NIST Chemistry Reference: 5 · 5-Methoxytryptamine(608-07-1)
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302
Precautionary statements: 301 · P301+P312+P330
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xn
Risk Statements: 22 · 22-36/37/38-20/21/22
Safety Statements: 36 · 36-26
WGK Germany: 3 · 3
RTECS: 4110000 · NL4110000
F: 8 · 8
HS Code: 29339900 · 29339900
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 Oral · Acute Tox. 4 Oral
Toxicity: 50 intraperitoneal · LD50 intraperitoneal in mouse: 176mg/kg
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 2% (1 of 49) of reports.

Warning

H302 (95.9%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 49 reports by companies from 5 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory InformationStatus: Active Update: 09-06-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/19684

Hazard Classes and CategoriesAcute Tox. 4 (95.9%)

Safety data

F: 8
PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
rtecs: NL4110000
hs_code: 29339900
Toxicity: LD50 intraperitoneal in mouse: 176mg/kg
risk_code: 22-36/37/38-20/21/22
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
safety_code: 36-26
Storage Class: 11 - Combustible Solids
Hazard statements: H302
REACH Registrations: Active
Hazard Classifications: Acute Tox. 4 Oral
Precautionary statements: P301+P312+P330

Chemistry & industry

Pharmacology

Metabolism/Metabolites5-methoxytryptamine has known human metabolites that include serotonin.

Tissue LocationsPlatelet

Applications · 3 items

Description5-Methoxytryptamine (5-MT), also known as mexamine, is a tryptamine derivative closely related to the neurotransmitters serotonin and melatonin. 5-MT has been shown to occur naturally in the body in low levels.It is biosynthesized via the deacetylation of melatonin in the pineal gland.The protective effect of 5-methoxytryptamine (a metabolite of melatonin) in human keratinocytes against ultraviolet B (UVB) radiation was studied.Melatonin and its metabolites ameliorate ultraviolet B-induced damage in human epidermal keratinocytes.

Uses5-Methoxytryptamine (Mexamine, Methoxytryptamine) is a tryptamine derivative that is closely related to the neurotransmitter Melatonin (M215000) and Serotonin (S274980). It acts as a full agonist at the 5-HT1, 5-HT2, 5-HT4, 5-HT6, and 5-HT7 receptors but has no affinity for the 5-HT3 receptor.

General DescriptionThe protective effect of 5-methoxytryptamine (a metabolite of melatonin) in human keratinocytes against ultraviolet B (UVB) radiation was studied.

Upstream & downstream products

Downstream products

2,3,4,9-tetrahydro-6-methoxy-1H-pyrido[3,4-b]indol-1-one 6-METHOXY-1,2,3,4-TETRAHYDRO-BETA-CARBOLINE 6-methoxy-1-phenyl-2,3,4,9-tetrahydro-1H-beta-carboline 6-METHOXY-1 2 3 4-TETRAHYDRO-9H-PYRIDO-&N-(2-nitrophenyl)-5-methoxytryptamine N-[2-(5-Methoxy-1H-indole-3-yl)ethyl]-2-chloroacetamide Melatonin

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

北京华美互利生物化工010-56205725 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

黄冈赛康药业有限公司[email protected]

Additional notes · 1 item

DefinitionChEBI: 5-methoxytryptamine is a member of the class of tryptamines that is the methyl ether derivative of serotonin. It has a role as a serotonergic agonist, a human metabolite, a mouse metabolite, a 5-hydroxytryptamine 2A receptor agonist, a 5-hydroxytryptamine 2C receptor agonist, a 5-hydroxytryptamine 2B receptor agonist, an antioxidant, a radiation protective agent, a neuroprotective agent and a cardioprotective agent. It is a member of tryptamines, an aromatic ether and a primary amino compound. It derives from a serotonin. It is a conjugate base of a 5-methoxytryptamine(1+).