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Tropane is a
nitrogenNitrogen is a chemical element that has the symbol N, atomic number of 7 and atomic mass 14.00674 u. Elemental nitrogen is a colorless, odorless, tasteless, and mostly inert diatomic gas at standard conditions, constituting 78.08% by volume of Earth's atmosphere...
ous
bicyclicA bicyclic molecule is a molecule that features two fused rings. Bicyclic molecules occur widely in organic and inorganic compounds.Fusion of the rings can occur in three ways:...
organic compoundAn organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
. It is mainly known for a group of
alkaloidAlkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...
s derived from it (called
tropane alkaloidTropane alkaloids are a class of alkaloids and secondary metabolites that contain a tropane ring in their chemical structure...
s), which include, among others,
atropineAtropine is a naturally occurring tropane alkaloid extracted from deadly nightshade , Jimson weed , mandrake and other plants of the family Solanaceae. It is a secondary metabolite of these plants and serves as a drug with a wide variety of effects...
and
cocaineCocaine is a crystalline tropane alkaloid that is obtained from the leaves of the coca plant. The name comes from "coca" in addition to the alkaloid suffix -ine, forming cocaine. It is a stimulant of the central nervous system, an appetite suppressant, and a topical anesthetic...
. Both alkaloids contain
tropinoneTropinone 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.-Synthesis:...
from which tropane is a derivate. Tropane alkaloids occur in
plantPlants are living organisms belonging to the kingdom Plantae. Precise definitions of the kingdom vary, but as the term is used here, plants include familiar organisms such as trees, flowers, herbs, bushes, grasses, vines, ferns, mosses, and green algae. The group is also called green plants or...
s of the families
ErythroxylaceaeThe Erythroxylaceae is a family of flowering plants consisting of 4 genera and approximately 240 species. The best-known species is the coca plant , the source of the drug cocaine....
(including
cocaCoca, Erythroxylum coca, is a plant in the family Erythroxylaceae, native to western South America. The plant plays a significant role in many traditional Andean cultures...
) and
SolanaceaeSolanaceae are a family of flowering plants that include a number of important agricultural crops as well as many toxic plants. The name of the family comes from the Latin Solanum "the nightshade plant", but the further etymology of that word is unclear...
(including
mandrakeMandrake is the common name for members of the plant genus Mandragora, particularly the species Mandragora officinarum, belonging to the nightshades family...
,
henbaneHenbane , also known as stinking nightshade or black henbane, is a plant of the family Solanaceae that originated in Eurasia, though it is now globally distributed.-Toxicity and historical usage:...
,
deadly nightshadeAtropa belladonna or Atropa bella-donna, commonly known as Belladonna, Devil's Berries, Death Cherries or Deadly Nightshade, is a perennial herbaceous plant in the family Solanaceae, native to Europe, North Africa, and Western Asia. The foliage and berries are extremely toxic, containing tropane...
,
daturaDatura is a genus of nine species of vespertine flowering plants belonging to the family Solanaceae. Its precise and natural distribution is uncertain, owing to its extensive cultivation and naturalization throughout the temperate and tropical regions of the globe...
,
potatoThe potato is a starchy, tuberous crop from the perennial Solanum tuberosum of the Solanaceae family . The word potato may refer to the plant itself as well as the edible tuber. In the region of the Andes, there are some other closely related cultivated potato species...
,
tomatoThe word "tomato" may refer to the plant or the edible, typically red, fruit which it bears. Originating in South America, the tomato was spread around the world following the Spanish colonization of the Americas, and its many varieties are now widely grown, often in greenhouses in cooler...
).
The nitrogen bridge is between C-1 and C-5; two asymmetric carbons, but tropane is optically inactive due to symmetry.
8-Azabicyclo[3.2.1]octane (tropane without the 8-
methyl groupMethyl group is a functional group derived from methane, containing one carbon atom bonded to three hydrogen atoms —CH3. The group is often abbreviated Me. Such hydrocarbon groups occur in many organic compounds. The methyl group can be found in three forms: anion, cation and radical. The anion...
) is known as nortropane or nor-tropane.