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86-13-5 molecular structure
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(1R,5R)-3-(diphenylmethoxy)-8-methyl-8-azabicyclo[3.2.1]octane

ChemBase ID: 130
Molecular Formular: C21H25NO
Molecular Mass: 307.4293
Monoisotopic Mass: 307.19361443
SMILES and InChIs

SMILES:
O(C1C[C@@H]2N([C@H](CC2)C1)C)C(c1ccccc1)c1ccccc1
Canonical SMILES:
CN1[C@@H]2CC[C@@H]1CC(C2)OC(c1ccccc1)c1ccccc1
InChI:
InChI=1S/C21H25NO/c1-22-18-12-13-19(22)15-20(14-18)23-21(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18-21H,12-15H2,1H3/t18-,19-/m1/s1
InChIKey:
GIJXKZJWITVLHI-RTBURBONSA-N

Cite this record

CBID:130 http://www.chembase.cn/molecule-130.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1R,5R)-3-(diphenylmethoxy)-8-methyl-8-azabicyclo[3.2.1]octane
IUPAC Traditional name
benztropine
Brand Name
Akitan
Apo-Benztropine
Cobrentin
Cogentin
Cogentinol
PMS Benztropine
Synonyms
Benzatropina [INN-Spanish]
Benzatropine
Benzatropinum [INN-Latin]
Benztropine Mesylate
Benztropinum
Tropine Benzohydryl Ether
Benzatropine mesilate
Benztropine
CAS Number
86-13-5
PubChem SID
160963593
PubChem CID
6832

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 6832 external link
DrugBank DB00245 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 0.79359984  LogD (pH = 7.4) 2.0576518 
Log P 4.1854005  Molar Refractivity 94.2404 cm3
Polarizability 37.30829 Å3 Polar Surface Area 12.47 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 4.47  LOG S -5.41 
Solubility (Water) 1.21e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
Very soluble expand Show data source
Hydrophobicity(logP)
4.3 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00245 external link
Item Information
Drug Groups approved
Description Benzotropine is a centrally-acting, antimuscarinic agent used as an adjunct in the treatment of Parkinson’s disease. It may also be used to treat extrapyramidal reactions, such as dystonia and Parkinsonism, caused by antipsychotics (e.g. phenothiazines). Symptoms of Parkinson’s disease and extrapyramidal reactions arise from decreases in dopaminergic activity which creates an imbalance between dopaminergic and cholinergic activity. Anticholinergic therapy is thought to aid in restoring this balance leading to relief of symptoms. In addition to its anticholinergic effects, benztropine also inhibits the reuptake of dopamine at nerve terminals via the dopamine transporter. Benzotropine also produces antagonistic effects at the histamine H1 receptor.
Indication For use as an adjunct in the therapy of all forms of parkinsonism and also for use in the control of extrapyramidal disorders due to neuroleptic drugs.
Pharmacology Benztropine is an anticholinergic used in the symptomatic treatment of all etiologic groups of parkinsonism and drug-induced extrapyramidal reactions (except tardive dyskinesia). Benztropine possesses both anticholinergic and antihistaminic effects, although only the former has been established as therapeutically significant in the management of parkinsonism. Benztropine's anticholinergic activity is about equal to that of atropine. Benztropine also inhibits dopamine reuptake via the dopamine transporter at nerve terminals.
Toxicity Signs of overdose include confusion, nervousness, listlessness, hallucinations, dizziness; muscle weakness, ataxia, dry mouth, mydriasis, blurred vision, palpitations, tachycardia, elevated blood pressure, nausea, vomiting, dysuria, numbness of fingers, headache, delirium, coma, shock, convulsions, respiratory arrest, anhidrosis, hyperthermia, glaucoma, and constipation.
Affected Organisms
Humans and other mammals
Absorption Onset of action is 1-2 hours following oral administration. The onset of action is within minutes when administered by IM or IV injection.
Protein Binding ~95% to serum proteins
References
Wszola BA, Newell KM, Sprague RL: Risk factors for tardive dyskinesia in a large population of youths and adults. Exp Clin Psychopharmacol. 2001 Aug;9(3):285-96. [Pubmed]
van Harten PN, Hoek HW, Matroos GE, Koeter M, Kahn RS: Intermittent neuroleptic treatment and risk for tardive dyskinesia: Curacao Extrapyramidal Syndromes Study III. Am J Psychiatry. 1998 Apr;155(4):565-7. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

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  • • Wszola BA, Newell KM, Sprague RL: Risk factors for tardive dyskinesia in a large population of youths and adults. Exp Clin Psychopharmacol. 2001 Aug;9(3):285-96. Pubmed
  • • van Harten PN, Hoek HW, Matroos GE, Koeter M, Kahn RS: Intermittent neuroleptic treatment and risk for tardive dyskinesia: Curacao Extrapyramidal Syndromes Study III. Am J Psychiatry. 1998 Apr;155(4):565-7. Pubmed
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