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5-Methoxytryptamine

5-Methoxytryptamine structure

CAS No:
608-07-1
Formula:
C11H14N2O
Chemical Name:
5-Methoxytryptamine
Synonyms:
1H-Indole-3-ethanamine,5-methoxy-;Indole,3-(2-aminoethyl)-5-methoxy-;5-Methoxy-1H-indole-3-ethanamine;5-MOT;3-(2-Aminoethyl)-5-methoxyindole;Methoxytryptamine;5-Methoxytryptamine;Deacetylmelatonin;2-(5-Methoxyindol-3-yl)ethylamine;[2-(5-Methoxy-1H-indol-3-yl)ethyl]amine;NSC 56422;2-[5-(Methyloxy)-1H-indol-3-yl]ethanamine;2-(5-Methoxy-1H-indol-3-yl)ethanamine;5-MeOT;2-(5-Methoxy-1H-indol-3-yl)ethan-1-amine
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

White to tan crystalline powder

Solid

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+).|Serotonin derivative proposed as potentiator for hypnotics and sedatives.

5-Methoxytryptamine Basic Attributes

Molecular Weight：

190.246

Exact Mass：

190.24

EC Number：

210-153-7

UNII：

3VMW6141KC

NSC Number：

56422

DSSTox ID：

DTXSID60209638

HScode：

2933990090

Characteristics

PSA：

XLogP3：

1.34

Appearance：

Solid

Density：

1.460 g/cm³

Melting Point：

121.5 °C

Boiling Point：

165-170 °C @ Press: 0.1 Torr

Flash Point：

223.5±24.6 °C

Refractive Index：

1.656

Storage Conditions：

2-8ºC

Toxicity：

LD50 intraperitoneal in mouse: 176mg/kg

Collision Cross Section：

141.18 Å² [M-H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|143.3 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R22

safety instructions：

S36

RTECS Number：

NL4110000

Marks：

Xn:Harmful;

Stability/Shelf Life：

Stable at normal temperatures and pressures.

Precautionary statement(s)：

P301 + P312 + P330

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (97.87%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 48 companies from 5 notifications to the ECHA C&L Inventory.

Drug Information

Metabolism/Metabolites：

5-methoxytryptamine has known human metabolites that include serotonin.

MeSH Entry Terms：

5 Methoxytryptamine

5-Methoxytryptamine Use and Manufacturing

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. Reactant for preparation of:• ;Carboline disaccharide domain of shishijimicin A1• ;Melatonin analogs for the reduction of intraocular pressure2• ;5-HT4 receptor ligands3• ;inhibitors of sortase A and isocitrate lyase4• ;Therapeutic agents for treatment of ischemia/reperfusion (I/R) injury5• ;Aurora and epidermal growth factor receptor kinase inhibitors6• ;Agents for the treatment of human papillomavirus infection7• ;Manzamine analogues for the control of neuroinflammation and cerebral infections8• ;Inhibitors of pro-inflammatory cytokines9& 5HT agonist

Computed Properties

Molecular Weight:190.24
XLogP3:0.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:190.110613074
Monoisotopic Mass:190.110613074
Topological Polar Surface Area:51
Heavy Atom Count:14
Complexity:186
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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