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1-Pyrrolidinepropanol, a-cyclohexyl-a-phenyl-

Names

[ CAS No. ]:
77-37-2

[ Name ]:
1-Pyrrolidinepropanol, a-cyclohexyl-a-phenyl-

[Synonym ]:
Kemadrine
Arpicolin
Procyklidin
Spamol
1-cyclohexyl-1-phenyl-3-pyrrolidin-1-yl-propan-1-ol
1-Cyclohexyl-3-pyrrolidino-1-phenyl-propan-1-ol
Lergine
Elorine
1-cyclohexyl-1-phenyl-3-pyrrolidin-1-ylpropan-1-ol
Triciclidina
tricyclamol
Osnervan
1-Cyclohexyl-1-phenyl-3-pyrrolidino-propan-1-ol

Biological Activity

[Description]:

Procyclidine (Tricyclamol; (±)-Procyclidine), an anticholinergic agent, is a muscarinic receptor antagonist that also has the properties of an N-methyl-D-aspartate (NMDA) antagonist. Procyclidine can be used in studies of Parkinson's disease and related psychiatric disorders such as Soman-induced epilepsy[1][2].

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> iGluR
Signaling Pathways >> Neuronal Signaling >> mAChR
Signaling Pathways >> GPCR/G Protein >> mAChR
Research Areas >> Neurological Disease
Signaling Pathways >> Membrane Transporter/Ion Channel >> iGluR

[In Vivo]

Procyclidine (subcutaneous injection, 0.3-6.0 mg/kg) in combination with physostigmine (PhS) increases protection in a dose-dependent manner in rats and guinea pigs infected with soman and can prevent seizures altogether[1]. Animal Model: Male Sprague-Dawley rats, Dunkin-Hartley male guinea pigs[1] Dosage: 0.3-6.0 mg/kg Administration: Subcutaneous injection; once Result: Increased protection, resulting in 1.92, 2.24, 3.95 and 5.07 fold in rats, 3.00, 3.25, 4.50 and 4.70 fold in guinea pigs at the doses of 0.3, 1.0, 3.0 or 6.0 mg/kg, respectively. Protected the neurological integrity of the brain and prevented Soman-induced severe brain damage in the hippocampus, cortex, amygdala and thalamus.

[References]

[1]. Yun-Bae Kim, et al. Effects of combinational prophylactics composed of physostigmine and procyclidine on soman-induced lethality, seizures and brain injuries. Environ Toxicol Pharmacol. 2002 Jan;11(1):15-21.

[2]. Ulrich Ettinger, et al. Effects of procyclidine on eye movements in schizophrenia. Neuropsychopharmacology. 2003 Dec;28(12):2199-208.

Chemical & Physical Properties

[ Density]:
1.057 g/cm3

[ Boiling Point ]:
433.5ºC at 760 mmHg

[ Melting Point ]:
85.5-86.5°

[ Molecular Formula ]:
C19H29NO

[ Molecular Weight ]:
287.44000

[ Flash Point ]:
205.7ºC

[ Exact Mass ]:
287.22500

[ PSA ]:
23.47000

[ LogP ]:
3.87830

[ Index of Refraction ]:
1.554

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UY1925000
CHEMICAL NAME :
1-Pyrrolidinepropanol, alpha-cyclohexyl-alpha-phenyl-
CAS REGISTRY NUMBER :
77-37-2
BEILSTEIN REFERENCE NO. :
0088563
LAST UPDATED :
199612
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C19-H29-N-O
MOLECULAR WEIGHT :
287.49
WISWESSER LINE NOTATION :
T5NTJ A2XQR&- AL6TJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
131 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: -,291,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
60 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: -,291,1972

Synthetic Route

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Precursor & DownStream

Precursor

DownStream

Related Compounds