Tropine

Names

[ CAS No. ]:
120-29-6

[ Name ]:
Tropine

[Synonym ]:
(1R,5S)-8-Methyl-8-azabicyclo[3.2.1]octan-3-ol
8-Methyl-8-azabicyclo[3.2.1]octan-3-ol
Tropine
endo-Tropanol
TROPAN-3ALPHA-OL
3alpha-Tropanol
8-Azabicyclo[3.2.1]octan-3-ol, 8-methyl-
EINECS 204-384-2
MFCD00005551
8-Azabicyclo[3.2.1]octan-3-ol, 8-methyl-, (1R,5S)-
endo-8-Methyl-8-azabicyclo[3.2.1]octan-3-ol
tropinol
3-TROPANOL
TROPANOL

Biological Activity

[Description]:

Tropine is a secondary metabolite of Solanaceae plants, is an anticholinergic agent[1]. Tropine is a common intermediate in the synthesis of a variety of bioactive alkaloids, including hyoscyamine and scopolamine[2].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Neurological Disease

[References]

[1]. Grynkiewicz G, et al. Tropane alkaloids as medicinally useful natural products and their synthetic derivatives as new drugs.Pharmacol Rep. 2008 Jul-Aug;60(4):439-63.

[2]. Richter U, et al. Overexpression of tropinone reductases alters alkaloid composition in Atropa belladonna root cultures.J Exp Bot. 2005 Feb;56(412):645-52. Epub 2005 Jan 10.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
233.0±0.0 °C at 760 mmHg

[ Melting Point ]:
50-60 °C(lit.)

[ Molecular Formula ]:
C₈H₁₅NO

[ Molecular Weight ]:
141.211

[ Flash Point ]:
112.5±14.5 °C

[ Exact Mass ]:
141.115356

[ PSA ]:
23.47000

[ LogP ]:
-0.10

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.526

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
100 g/L (20 ºC)

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YM3875000

CHEMICAL NAME :: 1-alpha-H,5-alpha-H-Tropan-3-alpha-ol

CAS REGISTRY NUMBER :: 120-29-6

BEILSTEIN REFERENCE NO. :: 0080188

LAST UPDATED :: 199701

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C8-H15-N-O

MOLECULAR WEIGHT :: 141.24

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 :: 139 mg/kg

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

REFERENCE :: ANCPAC Annales de Chimie. (Masson et Cie, Paris, France) V.9-15, 1914-77. Volume(issue)/page/year: 7,537,1962

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >50 mg/kg

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

REFERENCE :: ANCPAC Annales de Chimie. (Masson et Cie, Paris, France) V.9-15, 1914-77. Volume(issue)/page/year: 7,537,1962

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R20/22

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
1544

[ WGK Germany ]:
3

[ RTECS ]:
YM3875000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Tropine dehydrogenase: purification, some properties and an evaluation of its role in the bacterial metabolism of tropine.

Biochem. J. 307 ( Pt 2) , 603-8, (1995)

Tropine dehydrogenase was induced by growth of Pseudomonas AT3 on atropine, tropine or tropinone. It was NADP(+)-dependent and gave no activity with NAD+. The enzyme was very unstable but a rapid puri...

The metabolism of atropine in man.

J. Pharm. Pharmacol. 38(10) , 781-4, (1986)

A metabolic pattern of atropine in man, based on the detection of radiolabelled products in urine by high performance liquid chromatography after administration of [3H]atropine sulphate to a normal vo...

Determination of nitrogen-15 isotope fractionation in tropine: evaluation of extraction protocols for isotope ratio measurement by isotope ratio mass spectrometry.

Rapid Commun. Mass Spectrom. 23(24) , 4031-7, (2009)

N-Demethylation of tropine is an important step in the degradation of this compound and related metabolites. With the purpose of understanding the reaction mechanism(s) involved, it is desirable to me...