Azacyclonol

Names

[ CAS No. ]:
115-46-8

[ Name ]:
Azacyclonol

[Synonym ]:
alpha,alpha-Diphenyl-4-piperidinomethanol
4-(α,α Diphenyl) piperidine methanol
Diphenyl(4-piperidinyl)methanol
a,a-Diphenyl-4-piperidinemethanol
γ-Pipradrol
MFCD00066980
Ataractan
4-Piperidinemethanol, α,α-diphenyl-
α,α-Diphenyl-4-piperidinemethanol
α-(4-Piperidyl)benzhydrol
azacyclonol
diphenyl(4-piperidyl)methanol
Psychosan
g-Pipradrol
diphenyl(piperidin-4-yl)methanol
α,α-Diphenyl-4-piperidinomethanol
Diphenyl (g-Pyridyl)carbinol
a-(4-Piperidyl)benzhydrol
4-(Diphenylhydroxymethyl)piperidine
EINECS 204-092-5
Calmeran

Biological Activity

[Description]:

Azacyclonol, also known as γ-pipradol, is a drug used to diminish hallucinations in psychotic individuals.Target: OthersAzacyclonol is a drug which is a so-called ataractive, or agent which diminishes hallucinations in psychotic individuals. The formation of Azacyclonol in human intestinal microsomes is linear with respect to time up to 60 min. The rates of formation of Azacyclonol increases linearly with microsomal protein concentration up to 2 mg/mL. The apparent Km and Vmax values of Azacyclonol are 0.82 μM and 60 pmol/min/mg protein in microsomes from human liver [1]. The formation of Azacyclonol and terfenadine alcohol from terfenadine is confirmed to be catalyzed predominantly by CYP3A(4) isozyme, and the ratio of the rate of terfenadine alcohol formation to that of Azacyclonol is 3:1 [2]. The amount of Azacyclonol eliminated renally increases on average 2-fold after rifampin dosing [3].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Neurological Disease

[References]

[1]. Raeissi, S.D., et al., Comparison of CYP3A activities in a subclone of Caco-2 cells (TC7) and human intestine. Pharm Res, 1997. 14(8): p. 1019-25.

[2]. Ling, K.H., et al., Metabolism of terfenadine associated with CYP3A(4) activity in human hepatic microsomes. Drug Metab Dispos, 1995. 23(6): p. 631-6.

[3]. Brown, D.A. and J.P. Quilliam, The effects of some centrally acting drugs on ganglionic transmission in the cat. Br J Pharmacol Chemother, 1964. 23(2): p. 241-56.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
445.5±40.0 °C at 760 mmHg

[ Melting Point ]:
160-163 °C

[ Molecular Formula ]:
C₁₈H₂₁NO

[ Molecular Weight ]:
267.365

[ Flash Point ]:
142.0±18.0 °C

[ Exact Mass ]:
267.162323

[ PSA ]:
32.26000

[ LogP ]:
3.25

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.584

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TN0470000

CHEMICAL NAME :: 4-Piperidinemethanol, alpha,alpha-diphenyl-

CAS REGISTRY NUMBER :: 115-46-8

BEILSTEIN REFERENCE NO. :: 0230221

LAST UPDATED :: 199612

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C18-H21-N-O

MOLECULAR WEIGHT :: 267.40

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 650 mg/kg

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

REFERENCE :: PSCBAY Psychopharmacology Service Center, Bulletin. (Bethesda, MD) V.1-3, 1961-65. For publisher information, see PSYBB9. Volume(issue)/page/year: 2,17,1963

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 220 mg/kg

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

REFERENCE :: PSCBAY Psychopharmacology Service Center, Bulletin. (Bethesda, MD) V.1-3, 1961-65. For publisher information, see PSYBB9. Volume(issue)/page/year: 2,17,1963

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 350 mg/kg

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

REFERENCE :: PSCBAY Psychopharmacology Service Center, Bulletin. (Bethesda, MD) V.1-3, 1961-65. For publisher information, see PSYBB9. Volume(issue)/page/year: 2,17,1963

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 177 mg/kg

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

REFERENCE :: PSCBAY Psychopharmacology Service Center, Bulletin. (Bethesda, MD) V.1-3, 1961-65. For publisher information, see PSYBB9. Volume(issue)/page/year: 2,17,1963

Safety Information

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S24/25

[ RTECS ]:
TN0470000

[ HS Code ]:
29333999

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%