5-Hydroxytryptamine

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Names

[ CAS No. ]:
50-67-9

[ Name ]:
5-Hydroxytryptamine

[Synonym ]:
5-Hydroxytryptamine
Antemovis
MFCD00055054
Serotonine
Thrombotonin
3-(2-Aminoethyl)-5-hydroxyindole
Antemoqua
3-(2-aminoethyl)-1H-indol-5-ol
5-HT
EINECS 200-058-9
Enteramine

Chemical & Physical Properties

[ Density]:
1.011 g/mL at 25 °C(lit.)

[ Boiling Point ]:
211-212 °C(lit.)

[ Melting Point ]:
22-23 °C(lit.)

[ Molecular Formula ]:
C₁₀H₁₂N₂O

[ Molecular Weight ]:
176.21500

[ Flash Point ]:
205 °F

[ Exact Mass ]:
176.09500

[ PSA ]:
62.04000

[ LogP ]:
2.07500

[ Index of Refraction ]:
n20/D 1.538(lit.)

[ Water Solubility ]:
0.5 g/100 mL (25 ºC)

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NM2450000

CHEMICAL NAME :: Indol-5-ol, 3-(2-aminoethyl)-

CAS REGISTRY NUMBER :: 50-67-9

BEILSTEIN REFERENCE NO. :: 0143524

LAST UPDATED :: 199709

DATA ITEMS CITED :: 27

MOLECULAR FORMULA :: C10-H12-N2-O

MOLECULAR WEIGHT :: 176.24

WISWESSER LINE NOTATION :: T56 BMJ D2Z GQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 285 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PSCBAY Psychopharmacology Service Center, Bulletin. (Bethesda, MD) V.1-3, 1961-65. For publisher information, see PSYBB9. Volume(issue)/page/year: 2,17,1963

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 30 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PSCBAY Psychopharmacology Service Center, Bulletin. (Bethesda, MD) V.1-3, 1961-65. For publisher information, see PSYBB9. Volume(issue)/page/year: 2,17,1963

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 60 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: MZUZA8 Meditsinskii Zhurnal Uzbekistana. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) No.1- 1957- Volume(issue)/page/year: (3),61,1985

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 160 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IJPPAZ Indian Journal of Physiology and Pharmacology. (All India Institute of Medical Sciences, Dept. of Physiology, Ansari Nagar, New Delhi 110 029, India) V.1- 1957- Volume(issue)/page/year: 17,31,1973

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 601 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - ataxia Gastrointestinal - hypermotility, diarrhea

REFERENCE :: FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 26,10,1963

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 81 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - convulsions or effect on seizure threshold

REFERENCE :: FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 26,10,1963

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 750 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 112,319,1957

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 250 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 8(1),122,1982

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 5 mg/kg

TOXIC EFFECTS :: Cardiac - other changes Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 26,10,1963

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 12800 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 168,373,1967 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 10 mg/kg

SEX/DURATION :: female 12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Specific Developmental Abnormalities - other developmental abnormalities

REFERENCE :: FKGCAR Fortschritte der Kiefer-und Gesichts-Chirurgie. (Georg Thieme Verlag, Postfach 732, D-7000 Stuttgart 1, Fed. Rep. Ger.) V.1- 1955- Volume(issue)/page/year: 21,226,1976

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 10 mg/kg

SEX/DURATION :: female 18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord) Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: ARPAAQ Archives of Pathology. (Chicago, IL) V.5(3)-50(3), 1928-50; V.70-99, 1960-75. For publisher information, see APLMAS. Volume(issue)/page/year: 81,257,1966

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 20 mg/kg

SEX/DURATION :: female 6 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)

REFERENCE :: ANREAK Anatomical Record. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1906/08- Volume(issue)/page/year: 196,71A,1980

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 110 mg/kg

SEX/DURATION :: female 1-22 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - body wall

REFERENCE :: JOPDAB Journal of Pediatrics. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63141) V.1- 1932- Volume(issue)/page/year: 63,394,1963

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 110 mg/kg

SEX/DURATION :: female 1-22 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Newborn - live birth index (measured after birth)

REFERENCE :: JOPDAB Journal of Pediatrics. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63141) V.1- 1932- Volume(issue)/page/year: 63,394,1963

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 10 mg/kg

SEX/DURATION :: female 13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 25,626,1975

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 100 mg/kg

SEX/DURATION :: male 5 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands

REFERENCE :: ENDOAO Endocrinology (Baltimore). (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21203) V.1- 1917- Volume(issue)/page/year: 71,827,1962

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 240 mg/kg

SEX/DURATION :: female 1-6 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

REFERENCE :: JOENAK Journal of Endocrinology. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1939- Volume(issue)/page/year: 26,85,1963

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 320 mg/kg

SEX/DURATION :: female 14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion

REFERENCE :: JOENAK Journal of Endocrinology. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1939- Volume(issue)/page/year: 26,85,1963

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 10 mg/kg

SEX/DURATION :: female 7-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

REFERENCE :: JPMSAE Journal of Pharmaceutical Sciences. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.50- 1961- Volume(issue)/page/year: 58,406,1969

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 10 mg/kg

SEX/DURATION :: female 11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - urogenital system

REFERENCE :: JPMSAE Journal of Pharmaceutical Sciences. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.50- 1961- Volume(issue)/page/year: 58,406,1969

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 1 mg/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - body wall Reproductive - Specific Developmental Abnormalities - Central Nervous System

REFERENCE :: JPMSAE Journal of Pharmaceutical Sciences. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.50- 1961- Volume(issue)/page/year: 58,406,1969

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 240 mg/kg

SEX/DURATION :: female 11-16 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: SCIEAS Science. (American Assoc. for the Advancement of Science, 1333 H St., NW, Washington, DC 20005) V.1- 1895- Volume(issue)/page/year: 131,1101,1960

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 10 mg/kg

SEX/DURATION :: female 7-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

REFERENCE :: JPMSAE Journal of Pharmaceutical Sciences. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.50- 1961- Volume(issue)/page/year: 58,406,1969 *** REVIEWS *** TOXICOLOGY REVIEW ARVPAX Annual Review of Pharmacology. (Palo Alto, CA) V.1-15, 1961-75. For publisher information, see ARPTDI. Volume(issue)/page/year: 5,447,1965 TOXICOLOGY REVIEW PRSMA4 Proceedings of the Royal Society of Medicine. (New York, NY) V.1-70, 1907-77. For publisher information, see JRSMD9. Volume(issue)/page/year: 62,317,1969 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X6095 No. of Facilities: 7 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 202 (estimated) No. of Female Employees: 195 (estimated)

Safety Information

[ Hazard Codes ]:
T,N,F

[ Risk Phrases ]:
R24/25:Toxic in contact with skin and if swallowed . R34:Causes burns. R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . R39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation

[ Safety Phrases ]:
S26-S36/37/39-S45-S61-S36/37-S16-S7

[ RIDADR ]:
UN 2261 6.1/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
ZE5600000

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1

[ HS Code ]:
29071400

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

5-Methoxy-3-indoleaceate
L-5-Hydroxytryptophan
2-butoxyethanol
1H-Indole-3-ethanamine,5-(phenylmethoxy)-
5-hydroxy-Nb-methoxycarbonyltryptamine
5-Benzyloxyindole
5-benzyloxygramine
1H-Indole-3-acetamide,5-(phenylmethoxy)-
2-[2-(5-hydroxy-1H-indol-3-yl)ethyl]isoindole-1,3-dione
BENZYL[2-(5-HYDROXYINDOL-3-YL)-ETHYL]CARBAMATE

DownStream

3-(2-aminoethyl)-4-[3-(2-aminoethyl)-5-hydroxy-1H-indol-4-yl]-1H-indol-5-ol
3-(2-Aminoethyl)-1H-indole-4,5-dione
Serotonin glucuronide
2-(5-hydroxy-1H-indol-3-yl)acetaldehyde
1H-Pyrido[3,4-b]indol-6-ol,2,3,4,9-tetrahydro-1-methyl-
3,4,5,6-tetrahydro-7-hydroxy-6-methyl-1H-azepino[5,4,3-cd]indole
1H-Indole-3-ethanamine,5-(phenylmethoxy)-
BENZYL[2-(5-HYDROXYINDOL-3-YL)-ETHYL]CARBAMATE
N-Acetylserotonin
Serotonin O-Sulfate

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Related Compounds

5-hydroxytryptamine
5-hydroxytryptamine
5-Hydroxytryptamine HCl
N-Cbz-5-hydroxytryptamine
5-Hydroxytryptamine sulfate
5-Hydroxytryptamine adipate
5-Ethyl-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid
3-chloromethyl-4-propyl-4H-1,2,4-triazole hydrochloride
3-(2-(4-(4-fluorophenyl)piperazin-1-yl)-2-oxoethyl)-6-(4-methoxyphenyl)pyrimidin-4(3H)-one
3-Hydroxy-1H-pyrrol-2(5H)-one
ethyl 2-(5-amino-1H-1,2,3-benzotriazol-1-yl)acetate
1-(3,5-Difluoro-2-hydroxyphenyl)-2,2,2-trifluoroethanone
2-(Aminomethyl)-1-hydroxynaphthalene
1-(2,2-Dimethylpropyl)-2-fluorobenzene
Fmoc-l-buthionine
1-ethyl-N-methyl-1H-pyrazol-5-amine

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