Cyproheptadine

Names

[ CAS No. ]:
129-03-3

[ Name ]:
Cyproheptadine

[Synonym ]:
cyproheptadiene
EINECS 204-928-9
Dronactin
Periactine
Periactinol
MFCD00242817
Eiproheptadine
Cyproheptadine
1-methyl-4-(5-dibenzo[a,e]cycloheptatrienylidene)piperidine
MK 141
4-(5H-Dibenzo[a,d][7]annulen-5-ylidene)-1-methylpiperidine
Periactin
Cypoheptadine
4-dibenzo[a,d]cyclohepten-5-ylidene-1-methyl-piperidine
Periactin(R)

Biological Activity

[Description]:

Cyproheptadine is a potent and orally active 5-HT2A receptor antagonist, with antidepressant and antiserotonergic effects. Cyproheptadine has antiplatelet and thromboprotective activities. Cyproheptadine can be used for the research of thromboembolic disorders[1][2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cardiovascular Disease

Research Areas >> Neurological Disease

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor

Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

[In Vitro]

Cyproheptadine (0.01-100 nM; 1 minute) dose-dependently inhibits serotonin-enhanced ADP-induced mouse platelet aggregation in vitro[2]. Cyproheptadine (10 nM) has the ability to inhibit 15 µM serotonin-enhanced ADP-induced (1 µM) tyrosine phosphorylation in platelets in vitro[2]. Cyproheptadine inhibits human platelet PS exposure (Annexin V), P-selectin, and GPIIb-IIIa (PAC-1 binding) activation in vitro[2].

[In Vivo]

Cyproheptadine (1 mg/kg; i.p.; daily, for 5 days; C57BL/6 mice) exerts thromboprotective properties in vivo[2]. Animal Model: C57BL/6 mice (8-10 weeks old)[2] Dosage: 1 mg/kg Administration: Intraperitoneal injection; daily, for 5 days Result: Prolonged occlusion times and tail bleeding times in mice.

[References]

[1]. Calka O, et, al. Effect of cyproheptadine on serum leptin levels. Adv Ther, 2005. 22(5): p. 424-8.

[2]. Olivia A Lin, et al. The Antidepressant 5-HT2A Receptor Antagonists Pizotifen and Cyproheptadine Inhibit Serotonin-Enhanced Platelet Function. PLoS One. 2014; 9(1): e87026.

Chemical & Physical Properties

[ Density]:
1.115g/cm3

[ Boiling Point ]:
440.1ºC at 760mmHg

[ Melting Point ]:
298 °C (dec.)(lit.)

[ Molecular Formula ]:
C₂₁H₂₂ClN

[ Molecular Weight ]:
323.85900

[ Flash Point ]:
194.5ºC

[ Exact Mass ]:
323.14400

[ PSA ]:
3.24000

[ LogP ]:
5.43780

[ Vapour Pressure ]:
6.03E-08mmHg at 25°C

[ Index of Refraction ]:
1.5339 (20ºC)

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TM7000000

CHEMICAL NAME :: Piperidine, 4-(5H-dibenzo(a,d)cyclohepten-5-ylidene)-1-methyl-

CAS REGISTRY NUMBER :: 129-03-3

BEILSTEIN REFERENCE NO. :: 1685976

LAST UPDATED :: 199706

DATA ITEMS CITED :: 12

MOLECULAR FORMULA :: C21-H21-N

MOLECULAR WEIGHT :: 287.43

WISWESSER LINE NOTATION :: L C676 BYJ BU- DT6N DYTJ A1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 295 mg/kg

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

REFERENCE :: 27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,69,1972

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 52 mg/kg

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

REFERENCE :: 27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,69,1972

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 106 mg/kg

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

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 25,1723,1975

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 43300 ug/kg

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

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 25,1723,1975

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 107 mg/kg

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

REFERENCE :: 27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,69,1972

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 15 mg/kg

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

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 25,1723,1975

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 50 mg/kg

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

REFERENCE :: 27ZIAQ "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973 Volume(issue)/page/year: -,82,1973

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 3500 ug/kg

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

REFERENCE :: 27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,69,1972 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 10 mg/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4)

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: 257,168,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 20 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)

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: 257,168,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 20 mg/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)

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: 257,168,1982

Safety Information

[ Packaging Group ]:
I; II; III

[ HS Code ]:
29143900

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933399090

[ Summary ]:
2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%