Oxitriptan

HCID 439280

Completing data — usually done within a minute

Basic information

CAS
4350-09-8
Standard SMILES
N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O
InChIKey
LDCYZAJDBXYCGN-VIFPVBQESA-N
Molecular formula
C11H12N2O3
Average molar mass
220.22 g/mol
Monoisotopic mass
220.08479224

Overview

L-5-hydroxytryptophan appears as colorless to pale pink crystals. (NTP, 1992)

Names & identifiers

Preferred name
Oxitriptan
IUPAC
(2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid

Names & synonyms

oxitriptanLevothymPretonineQuietimTripteneOxyfanLevotinineSerotonylTelesolOxitriptanoOxitriptanumTripten
Show more names
(S)-5-HydroxytryptophanC1LJO185Q9CCRIS 4418EINECS 224-411-1Oxitriptanum [INN-Latin]Oxitriptano [INN-Spanish]BRN 0088200UNII-C1LJO185Q9

Database identifiers

CAS
4350-09-8
PubChem CID
439280
DTXSID
DTXSID1025437
ChEMBL
CHEMBL350221
ChEBI
CHEBI:17780
UNII
C1LJO185Q9
EC Number
224-411-1
Nikkaji
J4.572A

Properties

Computed structural propertiesFilling in

XLogP
-1.2
Topological polar surface area
99.3 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
4
Rotatable bonds
3
Heavy atoms
16

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LogP-2.051
Solubility · 2 items

Slightly soluble (NTP, 1992)

32.6 [ug/mL] (The mean of the results at pH 7.4)

Dietary IngredientsHydroxytryptophan (5-HTP)
Melting Point · 3 items

518 °F (decomposes) (NTP, 1992)

295-297

293 - 298 °C

Physical Description · 2 items

L-5-hydroxytryptophan appears as colorless to pale pink crystals. (NTP, 1992)

Solid

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301 (97.3%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 112 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationOxitriptan: Does not have an individual approval but may be used under an appropriate group standard
DOT LabelPoison
Fire HazardsFlash point data for this compound are not available, however, it is probably combustible. (NTP, 1992)
Health HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Reactive GroupPhenols and Cresols
Reactivity ProfileL-5-HYDROXYTRYPTOPHAN reacts with bases. (NTP, 1992).

Safety & protection

Fire FightingFires involving this compound can be controlled using dry chemical, carbon dioxide or Halon extinguishers. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, you should dampen the solid spill material with alcohol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with alcohol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminate area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Personal Protective Equipment (PPE) · 1 item

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Toxicology

Health EffectsChronically high levels of 5-hydroxytryptophan are associated with Aromatic L-Amino acid Decarboxylase Deficiency.
Toxicity Summary · 1 item

5-Hydroxy-L-tryptophan is the immediate precursor of the neurotransmitter serotonin. An accumulation of 5-hydroxy-L-tryptophan in cerebrospinal fluid occurs in aromatic L-amino acid decarboxylase deficiency, accompanied by an increased excretion in the urine of the patients, which are indicative of the disorder. 5-Hydroxy-L-tryptophan easily crosses the blood-brain barrier and effectively increases central nervous system (CNS) synthesis of serotonin. Supplementation with 5-hydroxy-L-tryptophan is hypothesized to normalize serotonin synthesis, which is putatively related to its antidepressant properties.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Chemistry & industry

Pharmacology

ATC Code · 2 items

N - Nervous system

QN - Nervous system

PharmacodynamicsThe psychoactive action of 5-HTP is thought to be due to increased serotonin production in central nervous system tissue.
Metabolism/Metabolites · 2 items

5-Hydroxytryptophan is decarboxylated to serotonin (5-hydroxytryptamine or 5-HT) by the enzyme aromatic-L-amino-acid decarboxylase via a vitamin B6 dependent reaction in nervous tissue and in the liver.

5-Hydroxytryptophan is decarboxylated to serotonin (5-hydroxytryptamine or 5-HT) by the enzyme aromatic-L-amino-acid decarboxylase with the help of vitamin B6. This reaction occurs both in nervous tissue and in the liver.

Tissue LocationsProstate
Cellular LocationsCytoplasm
Metabolite PathwaysTryptophan metabolism

Uses & manufacturing

UsesFor use as an antidepressant, appetite suppressant, and sleep aid.
General Manufacturing InformationL-Tryptophan, 5-hydroxy-: ACTIVE

Related reactions

8 records

Compound notes

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