2-methyl-9-phenyl-1H,2H,3H,4H,9H-indeno[2,1-c]pyridine

• ChemBase ID: 1395
• Molecular Formular: C19H19N
• Molecular Mass: 261.36086
• Monoisotopic Mass: 261.15174961
• SMILES: N1(CC2=C(CC1)c1c(C2c2ccccc2)cccc1)C
• Canonical SMILES: CN1CCC2=C(C1)C(c1ccccc1)c1c2cccc1
• InChI: InChI=1S/C19H19N/c1-20-12-11-16-15-9-5-6-10-17(15)19(18(16)13-20)14-7-3-2-4-8-14/h2-10,19H,11-13H2,1H3
• InChIKey: ISFHAYSTHMVOJR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methyl-9-phenyl-1H,2H,3H,4H,9H-indeno[2,1-c]pyridine
• IUPAC Traditional name: phenindamine; phenindamine tartrate
• Brand Name: Nolahist; Thephorin
• Synonyms: 2,3,4,9-Tetrahydro-2-methyl-9-phenyl-1H-indeno[2,1-c]pyridine Hydrochloride; 1,2,3,4-Tetrahydro-2-methyl-9-phenyl-2-azafluorene Hydrochloride; 2-Methyl-9-phenyl-2,3,4,9-tetrahydro-1-pyridindene Hydrochloride; Nu 1504; Thephorin Hydrochloride; Phenindamine Hydrochloride; Fenindamina [inn-spanish]; Phenindaminum [inn-latin]; Phenindiamine; Phenindamine

Database IDs

• CAS Number: 82-88-2; 5503-08-2
• PubChem SID: 160964855; 46508187
• PubChem CID: 11291

CALCULATED PROPERTIES

JChem

• Acid pKa: 18.006231
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.41971144
• LogD (pH = 7.4): 2.0139568
• Log P: 3.6197312
• Molar Refractivity: 85.0333 cm^3
• Polarizability: 32.8276 Å^3
• Polar Surface Area: 3.24 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.04
• LOG S: -3.97
• Solubility (Water): 2.77e-02 g/l

DETAILS

DrugBank - DB01619

• Drug Groups: approved
• Description: Phenindamine is an antihistamine. Phenindamine blocks the effects of the naturally occurring chemical histamine in your body. Antihistamines such as phenindamine appear to compete with histamine for histamine H1- receptor sites on effector cells. The antihistamines antagonize those pharmacological effects of histamine which are mediated through activation of H1- receptor sites and thereby reduce the intensity of allergic reactions and tissue injury response involving histamine release. It is used to treat sneezing, runny nose, itching, watery eyes, hives, rashes, itching, and other symptoms of allergies and the common cold.; Symptoms of a phenindamine overdose include extreme sleepiness, confusion, weakness, ringing in the ears, blurred vision, large pupils, dry mouth, flushing, fever, shaking, insomnia, hallucinations, and possibly seizures.
• Indication: Used to treat sneezing, runny nose, itching, watery eyes, hives, rashes, itching, and other symptoms of allergies and the common cold.
• Pharmacology: Phenindamine is an antihistamine. Phenindamine blocks the effects of the naturally occurring chemical histamine in your body. Allergies are caused by an excessive type 1 hypersensitivity response of the body to allergens, mediated by inappropriate histamine signalling. By inhibiting the binding of histamine, antihistamines decrease the normal histamine response from cells, consequently decreasing allergic symptoms.
• Toxicity: Symptoms of a phenindamine overdose include extreme sleepiness, confusion, weakness, ringing in the ears, blurred vision, large pupils, dry mouth, flushing, fever, shaking, insomnia, hallucinations, and possibly seizures.
• Affected Organisms: Humans and other mammals
• External Links: Drugs.com

Toronto Research Chemicals - P297000

Antihistaminic.

REFERENCES

• Lehmann G., et al.: J. Pharmacol. Exp. Ther., 92, 249 (1948)
• Cooper, J., et al.: Br. J. Cancer, 39, 87 (1948)
• Matthews, E., et al.: Regul. Toxicol. Pharmacol., 28, 242 (1948)