# Tropine > Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Tropine > Markdown URL: https://mediated.wiki/source/Tropine.md > Source: https://en.wikipedia.org/wiki/Tropine > Source revision: 1347365646 > License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/) {{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 444239133 | ImageFileL1 = Tropanol - tropine.svg | ImageClassL1 = skin-invert-image | ImageFileR1 = Tropine.png | ImageClassR1 = bg-transparent | PIN = (1''R'',3''r'',5''S'')-8-Methyl-8-azabicyclo[3.2.1]octan-3-ol | OtherNames = α-Tropine; Tropanol; 3-Tropanol | Section1 = {{Chembox Identifiers | CASNo_Ref = {{cascite|correct|??}} | CASNo = 120-29-6 | PubChem = 8424 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 7YXR19M72Y | MeSHName = Tropine | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 10180559 | SMILES = CN1[C@@H]2CC[C@H]1C[C@H](C2)O | InChI = 1/C8H15NO/c1-9-6-2-3-7(9)5-8(10)4-6/h6-8,10H,2-5H2,1H3/t6-,7+,8+ | InChIKey = CYHOMWAPJJPNMW-JIGDXULJBD | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C8H15NO/c1-9-6-2-3-7(9)5-8(10)4-6/h6-8,10H,2-5H2,1H3/t6-,7+,8+ | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = CYHOMWAPJJPNMW-JIGDXULJSA-N }} | Section2 = {{Chembox Properties | C=8|H=15|N=1|O=1 | Appearance = White [hygroscopic](/source/hygroscopic) crystalline powder{{cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/8424 | title=8-Methyl-8-azabicyclo[3.2.1]octan-3-ol }}{{Cite web | url=https://www.sigmaaldrich.com/GB/en/sds/aldrich/93550 | title=Safety Data Sheet - Tropine | website=www.sigmaaldrich.com}}{{cite web | url=https://www.merriam-webster.com/medical/tropine | title=Medical Definition of TROPINE }} or plates | Odor = [Amine](/source/Amine)-like | Density = 1.045 g/cm3 at 25 °C
1.016 g/cm3 at 100 °C | MeltingPtC = 64 | BoilingPtC = 233 | SolubleOther = Very soluble in water, [diethyl ether](/source/diethyl_ether), [ethanol](/source/ethanol){{Citation | last = Lide | first = David R. | author-link = | year = 1998 | title = Handbook of Chemistry and Physics | edition = 87 | volume = | series = | publication-place = Boca Raton, Florida | publisher = CRC Press | id = | isbn = 0-8493-0594-2 | doi = | oclc = | pages = 3–564 | url = | accessdate =}} }} | Section7 = {{Chembox Hazards | MainHazards = Toxic | LD50 = {{ubl|>2000 mg/kg (rat, oral)|139 mg/kg (mouse, intraperitoneal)|>50 mg/kg (rabbit, intravenous)|280 mg/kg (mouse, intraperitoneal)|>50 mg/kg (rabbit, intravenous)}} | GHSPictograms = {{GHS06}}{{GHS07}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|H301|H302|H312|H332}} | PPhrases = {{P-phrases|P261|P264|P270|P271|P280|P301+P316|P301+P317|P302+P352|P304+P340|P317|P321|P330|P362+P364|P405|P501}} }} }} '''Tropine''' is a derivative of [tropane](/source/tropane) containing a hydroxyl group at the third carbon. It is also called 3-tropanol. It is a poisonous white [hygroscopic](/source/hygroscopic) crystalline powder. It is a [heterocyclic](/source/heterocyclic) [alcohol](/source/Alcohol_(chemistry)) and an [amine](/source/amine). Tropine is a [central building block](/source/pharmacophore) of many chemicals active in the nervous system, including [tropane alkaloid](/source/tropane_alkaloid)s. Some of these compounds, such as [long-acting muscarinic antagonist](/source/long-acting_muscarinic_antagonist)s are used as medicines because of these effects.{{cite journal |last1=Ping |first1=Yu |last2=Li |first2=Xiaodong |last3=You |first3=Wenjing |last4=Li |first4=Guoqiang |last5=Yang |first5=Mengquan |last6=Wei |first6=Wenping |last7=Zhou |first7=Zhihua |last8=Xiao |first8=Youli |title=Production of the Plant-Derived Tropine and Pseudotropine in Yeast |journal=ACS Synthetic Biology |date=10 June 2019 |volume=8 |issue=6 |pages=1257–1262 |doi=10.1021/acssynbio.9b00152|pmid=31181154 |s2cid=184484993 }} ==Occurrence== Tropine is a natural product found in the plants of [deadly nightshade](/source/Atropa_bella-donna) (''Atropa belladonna'') and [devil's trumpet](/source/Datura_stramonium) (''Datura stramonium''). ==Chemistry== ===Synthesis=== It can be prepared by hydrolysis of [atropine](/source/atropine){{Cite web|url=https://www.seanmichaelragan.com/html/%5B2008-09-10%5D_Cocaine_analog_in_two_steps_from_native_plant_material.shtml|title=[2008-09-10] Cocaine analog in two steps from native plant material|website=www.seanmichaelragan.com}} or other [solanaceous](/source/solanaceous) [alkaloid](/source/alkaloid)s.{{cite journal | vauthors=Ladenburg, A | journal=Berichte der deutschen chemischen Gesellschaft | title=Bildung von Tropin aus Tropidin und die Synthese des Atropins | volume=35 | issue=1 | pages=1159–1162 | date= January 1902 | url=https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cber.190203501191 | doi=10.1002/cber.190203501191}} In the laboratory it is made by the reduction of [tropinone](/source/tropinone):{{cite journal | vauthors=Beckett, AH, Harper, NJ, Balon, ADJ, Watts, THE | journal=Tetrahedron | title=Stereochemistry of the reduction of tropinone | volume=6 | issue=4 | pages=319–330 | date= January 1959 | url=https://linkinghub.elsevier.com/retrieve/pii/0040402059800120 |doi=10.1016/0040-4020(59)80012-0| url-access=subscription }} Patent:Rolf Sachse & Albert Schaupp, {{US patent|6005110}} (1999 to Pfleger R Chemische Fabrik GmbH).Van de Kamp, Sletzinger, {{US patent|2366760}} (1945 to [Merck & Co.](/source/Merck_%26_Co.)) ==Derivatives== List of derivatives that can be made from [tropine](/source/tropine): #[AHN 1-055](/source/AHN_1-055) HCl: [202646-03-5]Newman, Amy Hauck; Allen, Andrew C.; Izenwasser, Sari; Katz, Jonathan L. (1994). "Novel 3.alpha.-(Diphenylmethoxy)tropane Analogs: Potent Dopamine Uptake Inhibitors without Cocaine-like Behavioral Profiles". Journal of Medicinal Chemistry. 37 (15): 2258–2261. doi:10.1021/jm00041a002.Newman, Amy Hauck; Kline, Richard H.; Allen, Andrew C.; Izenwasser, Sari; George, Clifford; Katz, Jonathan L. (1995). "Novel 4'-Substituted and 4',4-Disubstituted 3.alpha.-(Diphenylmethoxy)tropane Analogs as Potent and Selective Dopamine Uptake Inhibitors". Journal of Medicinal Chemistry. 38 (20): 3933–3940. doi:10.1021/jm00020a006. Patent:Amy Hauck Newman, {{US patent|5792775}} (1998 to US Department of Health and Human Services). Selfsame as [JHW-007](/source/JHW-007) (''N''-butyl group). This benzhydrol aromatic entity is the same as for flunamine & vanoxerine. #[Atropine](/source/Atropine)Al-Badr, A. A., Muhtadi, F. J. (1985). "Analytical Profiles of Drug Substances". Atropine. Vol. 14. Elsevier. pp. 325–389. doi:10.1016/S0099-5428(08)60585-7. #[Atromepine](/source/Atromepine)Melone, Gaetano; Vecchi, Alberto; Pagani, Giuseppe; Testa, Emilio (1960). "Notes- Tropine DL-α-Methyltropate (Methylatropine) and Its Optical Antipodes". The Journal of Organic Chemistry. 25 (5): 859–861. doi:10.1021/jo01075a624.Scarselli, Veniero; Cignarella, Giorgio; Maffii, Giulio (1964). "Structural Changes and Anticholinergic Activity in a Class of Tropic and α-Methyltropic Acid Derivatives". Journal of Medicinal Chemistry. 7 (2): 237–238. doi:10.1021/jm00332a026. #[Benztropine](/source/Benztropine)Richard P. Phillips, {{US patent|2595405}} (1952 to Merck a Co).Weijlard John, {{US patent|2706198}} (1952 to Merck & Co Inc). #[Bemesetron](/source/Bemesetron){{cite journal | vauthors=((Pento, J. T.)) | journal=Drugs of the Future | title=MDL-72222 | volume=10 | issue=10 | pages=820 | date= 1985 | url=http://journals.prous.com/journals/servlet/xmlxsl/pk_journals.xml_summary_pr?p_JournalId=2&p_RefId=61916&p_IsPs=N | issn=0377-8282 | doi=10.1358/dof.1985.010.10.61916 | access-date=8 December 2025| url-access=subscription }}John Richard Fozard, Maurice Ward Gittos, EP0067770 (1982 to Merrell Dow France Et Cie). #[Butropium bromide](/source/Butropium_bromide) (Coliopan®)Tanaka, Satoru; Wakabayashi, Tsuneo; Hashimoto, Kazunori; Toyoshima, Shoji (1972). "Studies on Diphenyl Ether Derivatives. III. : Synthesis and Spasmolytic Screening of New Quaternary Salts of Tropine Tropates". YAKUGAKU ZASSHI. 92 (4): 510–513. doi:10.1248/yakushi1947.92.4_510. DE1950378 idem Satoru Tanaka, Kazunori Hasimoto, US3696110 (1972 to Gisai Kk). #[Ciclotropium](/source/Ciclotropium) (wrong stereochemistry if employing this method) DE2026661 idem R Bauer, W Schulz, W Sirrenberg, G Walther US3743735 (1973 to Boehringer Sohn Ingelheim). #[Clobenztropine](/source/Clobenztropine)Fromer Stephen, FR1249205 (1961).Stephen Fromer, {{US patent|2799680}} (1957).Dr Stephan Fromer, DE1020634 (1957 to Schenley Lab Inc).Cyril H. Meld, {{US patent|2782200}} (1957 to Schenley Labora). #[https://pubchem.ncbi.nlm.nih.gov/#query=D-13264 D-13264]{{cite journal | vauthors=((Castañer, J.)), ((Thiemer, K.)), ((Klinger, K. H.)), ((Engel, J.)) | journal=Drugs of the Future | title=D-13,264 | volume=7 | issue=12 | pages=869 | date= 1982 | url=http://journals.prous.com/journals/servlet/xmlxsl/pk_journals.xml_summary_pr?p_JournalId=2&p_RefId=1003955&p_IsPs=N | issn=0377-8282 | doi=10.1358/dof.1982.007.12.1003955| url-access=subscription }} (atropine quat). #[Decitropine](/source/Decitropine) [1242-69-9]Dr August Franciscus Harms, DE1152410 (1963 to Koninklijke Pharma Fab Nv). #[Deptropine](/source/Deptropine){{cite journal | vauthors=((Van Der Stelt, C.)), ((Harms, A. F.)), ((Nauta, W. Th.)) | journal=Journal of Medicinal and Pharmaceutical Chemistry | title=The Effect of Alkyl-Substitution in Drugs--V. Synthesis and Chemical Properties of Some Dibenzo [a,d]1,4-cycloheptadienyl Ethers | volume=4 | issue=2 | pages=335–349 | date= September 1961 | url=https://pubs.acs.org/doi/abs/10.1021/jm50018a008 | doi=10.1021/jm50018a008| url-access=subscription }} Harms August Franciscus, {{US patent|3119829}} (1964 to Koninklijke Pharmaceutische Fabrieken NV). #[Fentonium](/source/Fentonium)Teotino, U.M . et al, Eur. J. Med. Chem .-Chim. Ther ., 1968, 3, 453 (synth, pharmacol), GB1026640 idem Davide Della Bella, Uberto Teotino, US3436458 (1969 to Whitefin Holding Sa). #[Flutropium bromide](/source/Flutropium_bromide) (wrong stereoisomer using this method of synthesis). DE2540633 idem Rolf Banholzer, Rudolf Bauer, Alex Heusner, Werner Schulz, {{US patent|4042700}} (1977 to Boehringer Ingelheim Gmbh). #[Homatropine](/source/Homatropine) Chemnitius, F. (1927). "Zur Darstellung des Homatropins". Journal für Praktische Chemie. 17 (1): 142–146. ISSN 0021-8383. doi:10.1002/prac.19271170105. #[PG-9](/source/PG-9) [156143-26-9] Maleate salt: [155649-00-6] Synthesis:{{cite journal | vauthors=((Gualtieri, F.)), ((Conti, G.)), ((Dei, S.)), ((Giovannoni, M. P.)), ((Nannucci, F.)), ((Romanelli, M. N.)), ((Scapecchi, S.)), ((Teodori, E.)), ((Fanfani, L.)), ((Ghelardini, C.)), ((Giotti, A.)), ((Bartolini, A.)) | journal=Journal of Medicinal Chemistry | title=Presynaptic Cholinergic Modulators as Potent Cognition Enhancers and Analgesic Drugs. 1. Tropic and 2-Phenylpropionic Acid Esters | volume=37 | issue=11 | pages=1704–1711 | date= May 1994 | url=https://pubs.acs.org/doi/abs/10.1021/jm00037a022 | doi=10.1021/jm00037a022}} Pharmacol:Ghelardini, Carla; Galeotti, Nicoletta; Bartolini, Alessandro; Furukawa, Shoei; Nitta, Atsumi; Manetti, Dina; Gualtieri, Fulvio (1998). "Memory Facilitation and Stimulation of Endogenous Nerve Growth Factor Synthesis by the Acetylcholine Releaser PG-9". The Japanese Journal of Pharmacology. 78 (3): 245–251. doi:10.1254/jjp.78.245. ISSN 0021-5198.Ghelardini C, Galeotti N, Gualtieri F, Marchese V, Bellucci C, Bartolini A. Antinociceptive and antiamnesic properties of the presynaptic cholinergic amplifier PG-9. J Pharmacol Exp Ther. 1998;284(3):806-16. PMID: 9495837.Ghelardini, C., Galeotti, N., Romanelli, M. N., Gualtieri, F., Bartolini, A. (March 2000). "Pharmacological Characterization of the Novel ACh Releaser α‐tropanyl 2‐(4‐bromophenyl)propionate (PG‐9)". CNS Drug Reviews. 6 (1): 63–78. doi:10.1111/j.1527-3458.2000.tb00138.x. #[Methoxytropacin](/source/Methoxytropacin) HCl: [74051-44-8] #[Prampine](/source/Prampine) [7009-65-6]{{Citation needed|date=December 2025}} #[Pudafensine](/source/Pudafensine)Dan Peters, et al. WO2011092061 (to NTG Nordic Transport Group AS). (by Mitsunobu inversion chemistry) #[SM-21](/source/SM-21) (other codenames covered too){{cite journal | vauthors=((Romanelli, M. N.)), ((Bartolini, A.)), ((Bertucci, C.)), ((Dei, S.)), ((Ghelardini, C.)), ((Giovannini, M. G.)), ((Gualtieri, F.)), ((Pepeu, G.)), ((Scapecchi, S.)), ((Teodori, E.)) | journal=Chirality | title=Synthesis and enantioselectivity of the enantiomers of PG9 and SM21, new potent analgesic and cognition-enhancing drugs | volume=8 | issue=3 | pages=225–233 | date= 1996 | url=https://onlinelibrary.wiley.com/doi/10.1002/(SICI)1520-636X(1996)8:3<225::AID-CHIR1>3.0.CO;2-G | doi=10.1002/(SICI)1520-636X(1996)8:3<225::AID-CHIR1>3.0.CO;2-G| url-access=subscription }}Alessandro Bartolini, et al. WO1994001435 (Abiogen Pharma SRL). #[SM-25](/source/SM-25) is the ester between tropine and [clofibric acid](/source/clofibric_acid). #[Tropabazate](/source/Tropabazate){{Citation needed|date=December 2025}} #[Tropacine](/source/Tropacine)Basel Gesellschaft Fuer Chemis [ch], CH202181 (1939 to Ciba), C.A. 33, 89228(1939).Friess, S.L.; Reber, L.J.; Thommesen, W.C.; Greenbaum, L.J.; Standaert, F.G.; Hudak, W.V. (1960). "Toxicologic properties and stereochemical configuration in derivatives of the tropanol series". Toxicology and Applied Pharmacology. 2 (5): 574–588. ISSN 0041-008X. doi:10.1016/0041-008X(60)90024-7.XU, Rong; SIM, Meng-Kwoon; GO, Mei-Lin (1998). "Synthesis, Antimuscarinic Activity and Quantitative Structure-Activity Relationship (QSAR) of Tropinyl and Piperidinyl Esters". CHEMICAL & PHARMACEUTICAL BULLETIN. 46 (2): 231–241. doi:10.1248/cpb.46.231. #[Tropacocaine](/source/Tropacocaine) (by Mitsunobu inversion chemistry) #[Tropanserin](/source/Tropanserin) J. R. Fozard and M. W. Gittos, US4563465 (1986 to Merrell Dow Pharmaceuticals Inc.)Fozard John Richard; Gittos Maurice Ward +, GB2131420 (1984 to Merrell Toraude & Co +); CA, 101,230355 #[Tropatepine](/source/Tropatepine) DE1952206 idem J Boissier, R Ratouis, US3725415 (1973 to Ind Pour La Fab Antibiotiques). #[Tropine benzilate](/source/Tropine_benzilate) ("BAT") #[Tropirine](/source/Tropirine) Harms, A. F., Chim. Ther., 1968, 3, 277. van der Stelt C, Hofman PS, Funcke AB, Nauta WT. Synthesis and pharmacological properties of some 5H-benzo(4,5)cyclohepta(1,2-b)pyridine derivatives. Arzneimittelforschung. 1968 Jun;18(6):756-8. PMID: 4387811. #[Tropodifene](/source/Tropodifene) Fedosowa; Magidson Zhurnal Obshchei Khimii, 1956 , vol. 26, p. 3475, 3477; engl. Ausg. S. 3867, 3868. #[Xenytropium](/source/Xenytropium)Laszlo Gyermek, {{US patent|2833773}} (1958). #[Zepastine](/source/Zepastine) Abraham Weber, Jacques Jean Frossard, {{US patent|3700663}} (1972 to Mead Johnson & Co). #3-Perfluorophenoxytropane ([https://pubchem.ncbi.nlm.nih.gov/compound/14575207 PC14575207])Grover C. Helsley, Larry Davis, Gordon E. Olsen, {{US patent|4861889}} (1989 to Hoechst-Roussel Pharmaceuticals, Inc.). #[https://pubchem.ncbi.nlm.nih.gov/compound/46905316 PC46905316] ([Ibuprofen](/source/Ibuprofen)) &[https://pubchem.ncbi.nlm.nih.gov/compound/16115711 PC16115711] ([Naproxen](/source/Naproxen)).{{Citation needed|date=December 2025}} #Tropine p-chlorophenoxyacetate [6658-61-3]{{cite journal | vauthors = Zakharevskiĭ AS, Shadurskiĭ KS | title = [Pharmacological properties of some p-chlorophenoxyacetic acid derivatives] | language = Russian | journal = Farmakologiia I Toksikologiia | volume = 38 | issue = 2 | pages = 154–9 | date = 1975 | pmid = 1227878 | doi = | url = }} (c.f. [Meclofenoxate](/source/Meclofenoxate)). == See also == * [Atropine](/source/Atropine) * [Pseudotropine](/source/Pseudotropine) * [Scopine](/source/Scopine) * [Tropane alkaloid](/source/Tropane_alkaloid) * [Tropinone](/source/Tropinone) == References == {{reflist}} Category:Tropanes Category:Secondary alcohols --- Adapted from the Wikipedia article [Tropine](https://en.wikipedia.org/wiki/Tropine) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Tropine?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.