Tropine

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Tropine
Alpha-Tropanol.svg
Tropine.png
Names
Preferred IUPAC name
(1R,3r,5S)-8-Methyl-8-azabicyclo[3.2.1]octan-3-ol
Other names
α-Tropine; Tropanol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.986 OOjs UI icon edit-ltr-progressive.svg
MeSH Tropine
PubChem CID
UNII
  • InChI=1S/C8H15NO/c1-9-6-2-3-7(9)5-8(10)4-6/h6-8,10H,2-5H2,1H3/t6-,7+,8+ X mark.svgN
    Key: CYHOMWAPJJPNMW-JIGDXULJSA-N X mark.svgN
  • 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
  • CN1[C@@H]2CC[C@H]1C[C@H](C2)O
Properties
C8H15NO
Molar mass 141.214 g·mol−1
AppearanceWhite 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:
GHS-pictogram-skull.svg GHS-pictogram-exclam.svg
Danger
H301, H302, H312, H332
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):
  • >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).
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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]

Contents

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

Related Research Articles

<i>Datura stramonium</i> Species of flowering plant in the nightshade family Solanaceae

Datura stramonium, known by the common names thorn apple, jimsonweed, devil's snare, or devil's trumpet, is a poisonous flowering plant of the nightshade family Solanaceae. It is a species belonging to the Datura genus and Daturae tribe. Its likely origin was in Central America, and it has been introduced in many world regions. It is an aggressive invasive weed in temperate climates and tropical climates across the world. D. stramonium has frequently been employed in traditional medicine to treat a variety of ailments. It has also been used as a hallucinogen, taken entheogenically to cause intense, sacred or occult visions. It is unlikely ever to become a major drug of abuse owing to effects upon both mind and body frequently perceived as being highly unpleasant, giving rise to a state of profound and long-lasting disorientation or delirium with a potentially fatal outcome. It contains tropane alkaloids which are responsible for the psychoactive effects, and may be severely toxic.

<span class="mw-page-title-main">Atropine</span> Anticholinergic medication used as antidote for nerve agent poisoning

Atropine is a tropane alkaloid and anticholinergic medication used to treat certain types of nerve agent and pesticide poisonings as well as some types of slow heart rate, and to decrease saliva production during surgery. It is typically given intravenously or by injection into a muscle. Eye drops are also available which are used to treat uveitis and early amblyopia. The intravenous solution usually begins working within a minute and lasts half an hour to an hour. Large doses may be required to treat some poisonings.

<i>Atropa belladonna</i> Species of toxic flowering plant in the nightshade family.

Atropa belladonna, commonly known as belladonna or deadly nightshade, is a toxic perennial herbaceous plant in the nightshade family Solanaceae, which also includes tomatoes, potatoes and aubergine (eggplant). It is native to Europe and Western Asia, including Turkey. Its distribution extends from Ireland in the west to western Ukraine and the Iranian province of Gilan in the east. It is also naturalised or introduced in some parts of Canada, North Africa and the United States.

<span class="mw-page-title-main">Hyoscyamine</span> Tropane alkaloid

Hyoscyamine is a naturally occurring tropane alkaloid and plant toxin. It is a secondary metabolite found in certain plants of the family Solanaceae, including henbane, mandrake, angel's trumpets, jimsonweed, the sorcerers' tree, and Atropa belladonna. It is the levorotary isomer of atropine and thus sometimes known as levo-atropine.

<span class="mw-page-title-main">Tropinone</span> Chemical compound

Tropinone is an alkaloid, famously synthesised in 1917 by Robert Robinson as a synthetic precursor to atropine, a scarce commodity during World War I. Tropinone and the alkaloids cocaine and atropine all share the same tropane core structure. Its corresponding conjugate acid at pH 7.3 major species is known as tropiniumone.

Tropane is a nitrogenous bicyclic organic compound. It is mainly known for the other alkaloids derived from it, which include atropine and cocaine, among others. Tropane alkaloids occur in plants of the families Erythroxylaceae and Solanaceae.

<span class="mw-page-title-main">Ecgonine</span> Chemical compound

Ecgonine is a tropane alkaloid found naturally in coca leaves. It has a close structural relation to cocaine: it is both a metabolite and a precursor, and as such, it is a controlled substance in many jurisdictions, as are some substances which can be used as precursors to ecgonine itself.

In enzymology, a tropinone reductase I (EC 1.1.1.206) is an enzyme that catalyzes the chemical reaction

In enzymology, a tropinone reductase II (EC 1.1.1.236) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Tropane alkaloid</span> Class of chemical compounds

Tropane alkaloids are a class of bicyclic [3.2.1] alkaloids and secondary metabolites that contain a tropane ring in their chemical structure. Tropane alkaloids occur naturally in many members of the plant family Solanaceae. Certain tropane alkaloids such as cocaine and scopolamine are notorious for their psychoactive effects, related usage and cultural associations. Particular tropane alkaloids such as these have pharmacological properties and can act as anticholinergics or stimulants.

<span class="mw-page-title-main">Anisodamine</span> Chemical compound

Anisodamine, also known as 7β-hydroxyhyoscyamine, is an anticholinergic and α1 adrenergic receptor antagonist used in the treatment of acute circulatory shock in China. It is given orally or by injection, as a racemic mixture (racanisodamine) or as a hydrobromide salt. Eye drops at 0.5% concentration for slowing the progression of myopia is also available in China.

<span class="mw-page-title-main">Methylatropine</span> Chemical compound

Methylatropine is a belladonna derivative.

<i>Bruguiera exaristata</i> Species of flowering plant

Bruguiera exaristata, commonly known as the rib-fruited mangrove or rib-fruited orange mangrove, is a mangrove of the family Rhizophoraceae.

<span class="mw-page-title-main">Tropacocaine</span> Chemical compound

Tropacocaine is a cocaine-related alkaloid and a contaminant of street cocaine.

<span class="mw-page-title-main">Littorine</span> Chemical compound

Littorine is a tropane alkaloid found in a variety of plants including Datura and Atropa belladonna. It is closely related in chemical structure to atropine, hyoscyamine, and scopolamine, which all share a common biosynthetic pathway.

Tropine acyltransferase is an enzyme with systematic name acyl-CoA:tropine O-acyltransferase. This enzyme catalyses the following chemical reaction

Pseudotropine acyltransferase is an enzyme with systematic name acyl-CoA:pseudotropine O-acyltransferase. This enzyme catalyses the following chemical reaction

<span class="mw-page-title-main">Apoatropine</span> Chemical compound

Apoatropine (atropatropine) is a member of class of tropane alkaloids. Chemically, it is an ester formed from tropine and atropic acid. Apoatropine can be found in plants of family Solanaceae. It is a bitter crystalline alkaloid. Examples of related tropane alkaloids include atropine, hyoscyamine, and hyoscine. Though apoatropine is found in various plants, it can also be prepared by the dehydration of atropine using nitric acid. Apoatropine is used as a pigment.

<span class="mw-page-title-main">Pseudotropine</span> Chemical compound

Pseudotropine is a derivative of tropane and an isomer of tropine. Pseudotropine can be found in the Coca plant along with several other alkaloids

<i>O</i>-Acylpseudotropine Class of chemical compounds

An O-acylpseudotropine is any derivative of pseudotropine in which the alcohol group is substituted with an acyl group.

References

  1. 1 2 3 "8-Methyl-8-azabicyclo[3.2.1]octan-3-ol".
  2. 1 2 3 4 https://www.sigmaaldrich.com/GB/en/sds/aldrich/93550
  3. 1 2 3 4 "Medical Definition of TROPINE".
  4. 1 2 Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, Florida: CRC Press, pp. 3–564, ISBN   0-8493-0594-2
  5. Ping, Yu; Li, Xiaodong; You, Wenjing; Li, Guoqiang; Yang, Mengquan; Wei, Wenping; Zhou, Zhihua; Xiao, Youli (10 June 2019). "Production of the Plant-Derived Tropine and Pseudotropine in Yeast". ACS Synthetic Biology. 8 (6): 1257–1262. doi:10.1021/acssynbio.9b00152. PMID   31181154. S2CID   184484993.
  6. "Cocaine analog in two steps from native plant material".