Tropine

Tropine is a derivative of tropane containing a hydroxyl group at the third carbon. It is also called 3-tropanol.^[4] It is a poisonous white hygroscopic crystalline powder.^[3] It is a heterocyclic alcohol and an amine.^[3]

Tropine

Names
Preferred IUPAC name (1R,3r,5S)-8-Methyl-8-azabicyclo[3.2.1]octan-3-ol
Other names α-Tropine; Tropanol
Identifiers
CAS Number	120-29-6 Y
3D model (JSmol)	Interactive image
ChemSpider	10180559 N
ECHA InfoCard	100.003.986
MeSH	Tropine
PubChem CID	8424
UNII	7YXR19M72Y Y
CompTox Dashboard (EPA)	DTXSID2049399
InChI InChI=1S/C8H15NO/c1-9-6-2-3-7(9)5-8(10)4-6/h6-8,10H,2-5H2,1H3/t6-,7+,8+ N Key: CYHOMWAPJJPNMW-JIGDXULJSA-N N InChI=1/C8H15NO/c1-9-6-2-3-7(9)5-8(10)4-6/h6-8,10H,2-5H2,1H3/t6-,7+,8+ Key: CYHOMWAPJJPNMW-JIGDXULJBD
SMILES CN1[C@@H]2CC[C@H]1C[C@H](C2)O
Properties
Chemical formula	C8H15NO
Molar mass	141.214 g·mol−1
Appearance	White hygroscopic crystalline powder[1][2][3] or plates
Odor	Amine-like[2]
Density	1.045 g/cm3 at 25 °C[2] 1.016 g/cm3 at 100 °C
Melting point	64 °C (147 °F; 337 K)
Boiling point	233 °C (451 °F; 506 K)
Solubility	Very soluble in water, diethyl ether, ethanol[4]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Toxic
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H302, H312, H332
Precautionary statements	P261, P264, P270, P271, P280, P301+P316, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P405, P501
Lethal dose or concentration (LD, LC):
LD50 (median dose)	>2000 mg/kg (rat, oral)[2] 139 mg/kg (mouse, intraperitoneal) >50 mg/kg (rabbit, intravenous) 280 mg/kg (mouse, intraperitoneal) >50 mg/kg (rabbit, intravenous)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Tropine is a central building block of many chemicals active in the nervous system, including tropane alkaloids. Some of these compounds, such as long-acting muscarinic antagonists are used as medicines because of these effects.^[5]

Occurrence

Tropine is a natural product found in the plants of deadly nightshade (Atropa belladonna) and devil's trumpet (Datura stramonium).^[1]

Chemistry

Synthesis

It can be prepared by hydrolysis of atropine^[6] or other solanaceous alkaloids.^[3]

See also

• Pseudotropine
• Atropine
• Tropinone
• Tropane alkaloid