1-methyl-4-{tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-ylidene}piperidine hydrochloride

• ChemBase ID: 73283
• Molecular Formular: C21H22ClN
• Molecular Mass: 323.85908
• Monoisotopic Mass: 323.14407739
• SMILES: C1(=C2CCN(CC2)C)c2c(C=Cc3c1cccc3)cccc2.Cl
• Canonical SMILES: CN1CCC(=C2c3ccccc3C=Cc3c2cccc3)CC1.Cl
• InChI: InChI=1S/C21H21N.ClH/c1-22-14-12-18(13-15-22)21-19-8-4-2-6-16(19)10-11-17-7-3-5-9-20(17)21;/h2-11H,12-15H2,1H3;1H
• InChIKey: ZPMVNZLARAEGHB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-methyl-4-{tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-ylidene}piperidine hydrochloride; 1-methyl-4-{tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,9,12,14-heptaen-2-ylidene}piperidine hydrochloride; 1-methyl-4-{tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-ylidene}piperidine hydrochloride; 1-methyl-4-{tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3,5,7,9,12,14-heptaen-2-ylidene}piperidine hydrochloride
• IUPAC Traditional name: 1-methyl-4-{tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-ylidene}piperidine hydrochloride; cyproheptadine hydrochloride; periactin hydrochloride
• Synonyms: Cyproheptadine; Periactin; Cyproheptadine hydrochloride; Periactin hydrochloride; 1-Methyl-4-(5-dibenzo(a,e)cycloheptatrienylidene) piperidinehydrochloride; 4-(5H-dibenzo[a,d][7]annulen-5-ylidene)-1-methylpiperidine hydrochloride; Piperidine, 4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-methyl-, hydrochloride, hydrate (2:3); Cyproheptadine hydrochloride sesquihydrate; 赛庚啶 盐酸盐 倍半水合物

Database IDs

• CAS Number: 969-33-5; 41354-29-4; 129-03-3
• EC Number: 213-535-1
• MDL Number: MFCD00012538
• PubChem SID: 162038203; 24278082
• PubChem CID: 13770

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.8782412
• LogD (pH = 7.4): 3.6462429
• Log P: 4.3828416
• Molar Refractivity: 105.1742 cm^3
• Polarizability: 36.445183 Å^3
• Polar Surface Area: 3.24 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: ethanol: soluble; methanol: soluble
• Apperance: white to slightly yellow solid
• Melting Point: 215-217°C

Safety Information

• Storage Condition: -20°C; Room Temperature (15-30°C)
• RTECS: TM7050000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22-36/37/38; R:22-36/37/38
• Safety Statements: 26-36; S:25-26-36/37/39
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Target: histamine
• Gene Information: human ... HRH1(3269), HTR2A(3356), HTR2B(3357), HTR2C(3358)
• Mechanism of Action: Cyproheptadine competes with free histamine for binding at HA-receptor sites.; This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding

Product Information

• Purity: ≥98% (TLC)
• Salt Data: HCl; hydrochloride
• Application(s): Antihistaminic and antiserotonergic agent
• Empirical Formula (Hill Notation): C21H21N·HCl·1.5H2O

DETAILS

MP Biomedicals - 02190170

Hydrochloride
Crystalline
Serotonin antagonist, antihistaminic and possibly a calcium channel blocker.

Selleck Chemicals - S2044

Research Area: Cancer
Biological Activity:

Sigma Aldrich - C6022

Biochem/physiol Actions
5-HT2/5-HT1C serotonin receptor antagonist; H1 histamine receptor antagonist; antipruritic.

REFERENCES

• Engelhardt, E.L. et al., J. Med. Chem., 1965, 8, 829, (synth, pharmacol)
• Aboul-Enein, H.Y. et al., Anal. Profiles Drug Subst., 1980, 9, 155, (rev)
• Fischer, L.J. et al., Drug Metab. Dispos., 1980, 8, 422, (metab)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6064, (synonyms)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 935
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, PCI250; PCI500