CAS 101-31-5: (-)-Atropine
Description:(-)-Atropine is a tropane alkaloid derived from plants of the Solanaceae family, particularly from belladonna (Atropa belladonna) and other related species. It is characterized by its chiral nature, existing as a single enantiomer, which is the (-)-form, known for its pharmacological activity. Atropine is a tertiary amine with a molecular formula of C17H23NO3 and a molecular weight of approximately 289.37 g/mol. It is a colorless to pale yellow crystalline solid that is soluble in organic solvents like alcohol and chloroform but has limited solubility in water. Atropine acts primarily as an anticholinergic agent, blocking the action of acetylcholine at muscarinic receptors, which leads to effects such as increased heart rate, dilation of pupils, and reduced secretions. It is used clinically to treat bradycardia, as an antidote for organophosphate poisoning, and to induce mydriasis during ophthalmic examinations. Due to its potent effects, atropine must be used with caution, as it can cause side effects such as dry mouth, blurred vision, and tachycardia.
Formula:C17H23NO3
InChI:InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16-/m1/s1
InChI key:InChIKey=RKUNBYITZUJHSG-FXUDXRNXSA-N
SMILES:O=C(OC1CC2N(C)C(CC2)C1)C(C=3C=CC=CC3)CO
- Synonyms:
- (-)-Atropine
- (1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl (2S)-3-hydroxy-2-phenylpropanoate
- (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl (2S)-3-hydroxy-2-phenylpropanoate
- (S)-(-)-Hyoscyamine
- (S)-Atropine
- 1α<span class="text-smallcaps">H</smallcap>,5α<smallcap>H</span>-Tropan-3α-ol, (-)-tropate (ester)
- 1α<span class="text-smallcaps">H</smallcap>,5α<smallcap>H</span>-Tropan-3α-yl (-)-tropate
- 1αH,5αH-Tropan-3α-ol, (-)-tropate (ester)
- 1αH,5αH-Tropan-3α-yl (-)-tropate
- 8-Methyl-8-Azabicyclo[3.2.1]Oct-3-Yl 3-Hydroxy-2-Phenylpropanoate
- See more synonyms
- 8-methyl-8-azabicyclo[3.2.1]oct-3-yl (2S)-3-hydroxy-2-phenylpropanoate
- <span class="text-smallcaps">L</span>-Hyoscyamin
- <span class="text-smallcaps">L</span>-Hyoscyamine
- Benzeneacetic acid, α-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, (αS)-
- Benzeneacetic acid, α-(hydroxymethyl)-, 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, [3(S)-endo]-
- Cystospaz
- Daturine
- Duboisine
- Hiosciamina
- Hyoscyamin
- L-Hyoscyamin
- L-Hyoscyamine
- L-Hyoscyamine free base
- Tropic acid, 1α<span class="text-smallcaps">H</smallcap>,5α<smallcap>H</span>-tropan-3α-yl ester, (-)-
- l-Atropine
- l-Tropine tropate
- Tropic acid, 1αH,5αH-tropan-3α-yl ester, (-)-