hyoscyamine

Also known as Tropine-L-tropate, Daturin, [3(S)-Endo]-alpha-(hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, (−)-atropine, (-)-Hyoscyamine, Daturine, L-Hyoscyamine, Duboisine

Hyoscyamine (also known as daturine or duboisine) 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 (deadly nightshade). It is the Levorotatory isomer of atropine.

Key facts

Drug.Verifiedfields: changed
Drug.verifiedrevid: 461742575
Drug.image: Hyoscyamine.svg
Drug.image_class: skin-invert-image
Drug.width: 200
Drug.image2: Hyoscyamine-from-xtal-3D-balls.png
Drug.image_class2: bg-transparent
Drug.tradename: Anaspaz, Levbid, Levsin
Drug.MedlinePlus: a684010
Drug.routes_of_administration: By mouth, Injection
Drug.ATC_prefix: A03
Drug.ATC_suffix: BA03
Drug.legal_AU: S4
Drug.legal_US: Rx only
Drug.bioavailability: 50% protein binding
Drug.metabolism: Liver
Drug.elimination_half life: 3–5 hrs.
Drug.excretion: Kidney

via Wikipedia infobox

Chemical data

Formula: C17H23NO3
Molecular weight: 289.4 g/mol
IUPAC name: [(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2S)-3-hydroxy-2-phenylpropanoate
SMILES: CN1[C@@H]2CC[C@H]1CC(C2)OC(=O)[C@H](CO)C3=CC=CC=C3
InChIKey: RKUNBYITZUJHSG-VFSICIBPSA-N
XLogP: 1.8
Polar surface area: 49.8 Å²
H-bond donors: 1
H-bond acceptors: 4
Formal charge: 0