erythroxylum coca alkaloids
2020 Sep 28;10(5):579-584. doi: 10.4103/jispcd.JISPCD_237_20. Coca grown in the Chapare Valley of Bolivia were subjected to gas and liquid chromatographic-mass spectrometric analyses. 2014 Apr;237:30-9. doi: 10.1016/j.forsciint.2014.01.012. The cultivated Erythroxylum varieties E. coca var. It has a potent stimulating action oncentral nervous system, producing a sense of euphoriaand increased energy. coca, E. coca var. Please enable it to take advantage of the complete set of features! ... Coca alkaloids; References Citations Sources. Erythroxylum coca var. We can incorporate these wonderful benefits of the coca leaf most often in tea form, however chewing the leaves is also a common practice. Variation of Alkaloid Content in Erythroxylum coca Leaves from Leaf Bud to Leaf Drop. The cocaine alkaloid content of dry Erythroxylum coca var. eCollection 2019. novogranatense are the two main cocaine-producing species. To determine whether tropane alkaloid formation in distant angiosperm lineages has a common evolutionary origin, we investigated the tropinone-reduction step in Erythroxylum coca (Erythroxylaceae), a species that accumulates cocaine and other tropane alkaloids in abundance and is taxonomically very remote from the Solanaceae. Clipboard, Search History, and several other advanced features are temporarily unavailable. 2019 Jun 4;116(23):11207-11212. doi: 10.1073/pnas.1902174116. Coca (Erythroxylum coca). Molecules. Coca alkaloid interferes with the transport of the neuro-transmitterdopamine. 2019 Nov 26;5:20. doi: 10.1186/s40794-019-0095-7. National Center for Biotechnology Information, Unable to load your collection due to an error, Unable to load your delegates due to an error. The cultivated Erythroxylum varieties E. coca var. The resulting crude extracts were analyzed by gas chromatography--mass spectrometry. The branches are straight, and the leaves, which have a green tint, are thin, opaque, oval, and taper at the extremities. coca leaves was measured ranging from 0.23 % to 0.96 %. Epub 2016 Apr 7. The cultivated Erythroxylum varieties E. coca var. And Erythroxylum novogranatense var. Coca grown in the Chapare Valley of Bolivia were subjected to gas and liquid chromatographic-mass spectrometric analyses. Determination and in-depth chromatographic analyses of alkaloids in South American and greenhouse-cultivated coca leaves. L. Rivier, “Analysis of alkaloids in leaves of cultivated Erythroxylum and characterization of alkaline substances used during coca chewing,” Journal of Ethnopharmacology, vol. Cocaine, commonly called as coke or crack. The biological activity of the following alkaloids has been reported in the literature: cocaine, … [1] They are predominantly of either the pyrrolidine or the tropane types. It is now a substance whose possession and trade is strictly controlled all over the world. Hardly anything is known about the biological activity of the other alkaloids present in the four varieties mentioned. Epub 2005 Jan 13. 2-3, pp. coca, E. coca var. The coca bush originated in the rain forests of the Andes, and has been cultivated in South American for many purposes for thousands of years. 3, no. USA.gov. Bot., 1994, volume 73, issue 6, pages 645-650, Learn how and when to remove this template message, https://en.wikipedia.org/w/index.php?title=Coca_alkaloid&oldid=1000331085, Articles needing additional references from July 2013, All articles needing additional references, Creative Commons Attribution-ShareAlike License, This page was last edited on 14 January 2021, at 17:45. Cocaine (from Erythroxylum coca) is a very potent local anesthetic. truxillense contain 18 alkaloids, identified so far, belonging to the tropanes, pyrrolidines and pyridines, with cocaine as the main alkaloid. Alternative Titles: Erythroxylum coca, Huanuco cocaine Coca, (Erythroxylum coca), tropical shrub, of the family Erythroxylaceae, the leaves of which are the source of the drug cocaine. 334 Johnson - Erythroxylum coca Leaf Alkaloid Distribution cinnamoylcocaine increased in the leaf, and by week 36 of leaf duration (at leaf drop) /rúTw-cinnamoylcocaine was the predominant leaf alkaloid (Johnson and Emche, 1994). The biosynthesis of the coca alkaloids has been outlined. coca and E. novogranatense var. coca. Several alkaloids from these seeds were detected and characterized, including methylecgonidine, tropine, 3alpha-acetoxytropane, ecgonine methyl ester, cuscohygrine, N-norbenzoyltropine, … Cocaine is the major alkaloid in both coca and novogranatense spe-cies, ranging from 0.3% to 1.5% (w/w), with an av-erage of 0.8% relative to leaf dry weight. Approach (from AD-416) Greenhouse-grown Erythroxylum coca var. Inter- and intra-specific variation among five Erythroxylum taxa assessed by AFLP. ipadu, E. novogranatense var. Erythroxylum coca, otherwise known as Coca or Little Coca, is an evergreen small tree growing up to 3.5 m tall. A DFT Study of the Photochemical Dimerization of Methyl 3-(2-Furyl)acrylate and Allyl Urocanate. It has been estimated that there are over 200 Erythroxylum species growing in the Western Hiisphere. The cultivated Erythroxylum varieties E. coca var. Prevention and treatment information (HHS). Epub 2019 May 6. Rivier L. Several solvents were tested for the extraction of the alkaloids in Erythroxylum coca. truxillense contain 18 alkaloids, identified so far, belonging to the tropanes, pyrrolidines and pyridines, with cocaine as the main alkaloid. Coca-Cola used coca leaf extract in its products from 1885 until about 1903. Several alkaloids from these seeds were detected and characterized, including methylecgonidine, tropine, 3alpha-acetoxytropane, Proc Natl Acad Sci U S A. novogranatense were localized using histochemical, cytochemical, and immunocytochemical probes. novogranatense (Morris) Hieron (E.n. Besides co- They are predominantly of either the pyrrolidine or the tropane types. At the tissue level, these alkaloids were localized in leaves, stems, and fruits with Dragendorff's reagent. The cultivated Erythroxylum varieties E. coca var. Coca alkaloid. From "Coca Cultivation and Cocaine Processing: An Overview" by DEA, Sept. 1993. Quinine (from Cinchona species) is a powerful antimalarial agent that was formerly the drug of choice for treating that disease, though it has been largely replaced by less toxic and more effective synthetic drugs. ipadu, E. novogranatense var. Coca: The History and Medical Significance of an Ancient Andean Tradition. Emerg Med Int. Coca alkaloids are the alkaloids found in the coca plant, Erythroxylum coca. 2019 Oct 21;24(20):3788. doi: 10.3390/molecules24203788. novogranatense and E. novogranatense var. 2016;2016:4048764. doi: 10.1155/2016/4048764. 1994 Jan 21;659(1):163-75. doi: 10.1016/0021-9673(94)85018-6. coca and Erythroxylum novogranatense var. 313–335, 1981. Analysis of alkaloids in leaves of cultivated Erythroxylum and characterization of alkaline substances used during coca chewing. ALKALOIDS IDENTIFIED IN THE FOUR VARIETIES OF CULTIVATED COCA - Other sources in Erythroxylum species Tropane alkaloids Cocaine (Wohler and Niemann, 1860) Cinnamoylcocaine (Giasel, 1889) cis-Cinnamoylcocaine (Moore, 1973) trans.Cinnamoylcocaine (Moore, (1973) Benzoylecgonine (Merck, 1885) Methylecgonine (de Jong, 1939) Coca grown in the Chapare Valley of Bolivia were subjected to gas and liquid chromatographic-mass spectrometric analyses. In the Peruvian lowlands, many pre-Colombian graves have been found to contain the remains of coca leaves, lime, and artifacts used for coca … Chemical evidence for the use of multiple psychotropic plants in a 1,000-year-old ritual bundle from South America. However, these compounds are usually separated by traditional chromatographic techniques, in which the sample is progressively purified in multiple chromatographic steps, resulting in a time‐ and … The earliest evidence of coca leaf chewing comes from about 3000 B.C.E. Ann Bot. NIH coca, E. coca var. Erythroxylum coca is one of two species of cultivated coca Description. eCollection 2020 Sep-Oct. Restrepo DA, Saenz E, Jara-Muñoz OA, Calixto-BotÃa IF, RodrÃguez-Suárez S, Zuleta P, Chavez BG, Sanchez JA, D'Auria JC. novogranatense (Morris) Hieron (E.n. Trop Dis Travel Med Vaccines. Erythroxylum coca leaves directly from Cuzco, ... Proteins, Minerals and Alkaloids are also present. Would you like email updates of new search results? Coca alkaloid or cocaine is obtained from coca plant Erythroxylum coca. Alkaloid extracts from the seeds of Erythroxylum Coca var. ipadu, E. novogranatense var. Fifteen of the 17 species contain relatively low levels of cocaine alkaloid and subsequently are not cultivated. The biological activity of the following alkaloids has been reported in the literature: cocaine, cinnamoylcocaine, benzoylecgonine, methylecgonine, pseudotropine, benzoyltropine, tropacocaine, alpha- and beta-truxilline, hygrine, cuscohygrine and nicotine. This site needs JavaScript to work properly. var. novogranatense) were grown in a controlled environment for 52 weeks to monitor the content of hygrine, tropinone, tropacocaine, methyl ecgonine, cocaine and cis - and trans -cinnamoylcocaine in seeds, plant parts, and organs during juvenile growth. Chemosystematic identification of fifteen new cocaine-bearing Erythroxylum cultigens grown in Colombia for illicit cocaine production. You are on www.phytomania.com French site dedicated to medicinal plants and essential oils | truxillense contain 18 alkaloids, identified so far, belonging to the tropanes, pyrrolidines and pyridines, with cocaine as the main alkaloid. Molecules. Oral use of the coca leaf continues to this day and is not associated with significant abuse. Forensic Sci Int. Alkaloid extracts from the seeds of Erythroxylum Coca var. And Erythroxylum novogranatense var. novogranatense and E. novogranatense var. It is commonly found in South America particularly in northern Brazil, Bolivia, and Peru. COVID-19 is an emerging, rapidly evolving situation. novogranatense and E. novogranatense var. HHS ipadu, E. novogranatense var. | Progress 10/01/06 to 09/30/07 Outputs Progress Report Objectives (from AD-416) Determine the effect of glyphosate applied at various levels below recommended field application rates for the control of Erythroxylum species on cocaine and other alkaloids produced in leaves 60 days and 150 days after treatment. coca, E. coca var. The Erythroxylum coca (scientific name of the plant) has proteins, Erythroxylum in Focus: An Interdisciplinary Review of an Overlooked Genus. 2005 Mar;95(4):601-8. doi: 10.1093/aob/mci062. Loyola D, Mendoza R, Chiong L, Rueda M, AlvÃtez-Temoche D, Gallo W, Mayta-Tovalino F. J Int Soc Prev Community Dent. Alkaloid extracts from the seeds of Erythroxylum Coca var. The leaves contain cocaine and other alkaloids. In addition to cocaine, the coca leaf contains many other alkaloids, including methylenehexine cinnamate, benzylekgoin, truxillin, hydroxytropacocaine, tropacocaine, ecgoin, couscogyrin, dihydrocuscogyrin, nicotine and hygrin. It has straight branches, thin leaves that are opaque and oval, and small flowers. Coca alkaloids are the alkaloids found in the coca plant, Erythroxylum coca. coca Lam. Despite the long history of cocaine use among humans and its social and economic significance today, little information is available about the biochemical and molecular aspects of cocaine biosynthesis in coca (Erythroxylum coca) in comparison to what is known about the formation of other pharmacologically-important tropane alkaloids in species of the Solanaceae. Coca grown in the Chapare Valley of Bolivia were subjected to gas and liquid chromatographic-mass spectrometric analyses. | Moore JM, Casale JF, Klein RF, Cooper DA, Lydon J. J Chromatogr A. Miller MJ, Albarracin-Jordan J, Moore C, Capriles JM. Travel medicine, coca and cocaine: demystifying and rehabilitating. ipadu, E. novogranatense var. novogranatense and E. novogranatense var. Fully expanded leaves of Erythroxylum coca var. Cocaine is a tropane ester alkaloid found in the leaves of the Erythroxylum coca plant, a bush that grows in the Andes region of South America. Tropane alkaloids are bioactive metabolites with great importance in the pharmaceutical industry and the most important class of natural products found in the Erythroxylum genus. Download PDF: Sorry, we are unable to provide the full text but you may find it at the following location(s): https://dspace.library.uu.nl/b... (external link) Alkaloid extracts from the seeds of Erythroxylum Coca var. Epub 2014 Jan 31. 2014 Dec 8;19(12):20482-20497. doi: 10.3390/molecules191220482. coca, E. coca var. from E. coca var. When chewed they produce a sense of warmth in the mouth and have a pleasant, pungent taste. Several alkaloids from these seeds were detected and characterized, including methylecgonidine, tropine, 3α-acetoxytropane, ecgonine methyl ester, cuscohygrine, N … The native people use it as a stimulant . Detection and Characterization of Cocaine and Related Tropane Alkaloids in Coca Leaf, Cocaine, and Biological Specimens. The coca plant resembles a blackthorn bush, and grows to a height of 2–3 m (7–10 ft). Alkaloids are a class of naturally occurring organic compounds that mostly contain basic nitrogen atoms. The tropane alkaloids of Erythroxylum coca var. [1] They are predominantly of either the pyrrolidine or the tropane types. var. NLM Coca alkaloids are the alkaloids found in the coca plant, Erythroxylum coca. Cocaine, extracted from coca leaves, is one of the first medical alkaloids used in medicine. truxillense contain 18 alkaloids, identified so far, belonging to the tropanes, pyrrolidines and pyridines, with cocaine as the main alkaloid. Conclusion. Only 17 species can be utilised for producing cocaine. truxillense contain 18 alkaloids, identified so far, belonging to the tropanes, pyrrolidines and pyridines, with cocaine as the main alkaloid. The pharmacologically active component of coca is the alkaloid cocaine, contained in an amount of 0.2-1% in fresh leaves. Emanuel L. Johnson and Stephen D. Emche, Ann. The biological activity of cocaine and nicotine is not reviewed here, because it is discussed elsewhere in the literature. novogranatense and E. novogranatense var. (Erythroxylaceae) 35-70-d-old were harvested from 21-month-old plants grown under greenhouse conditions. Its stimulant properties have been known to the indigenous population for at least 2000 years. 95 ( 4 ):601-8. doi: 10.4103/jispcd.JISPCD_237_20 intra-specific variation among five Erythroxylum assessed! E. coca var from the seeds of Erythroxylum coca Erythroxylum taxa assessed by AFLP are a class naturally... The tropane types occurring organic compounds that mostly contain basic nitrogen atoms Bud to erythroxylum coca alkaloids... ( 12 ):20482-20497. doi: 10.4103/jispcd.JISPCD_237_20 was measured ranging from 0.23 % to 0.96 % the tropane.! Has been outlined alkaloids were localized in leaves of cultivated coca Description mass spectrometry, is an evergreen small growing... A height of 2–3 m ( 7–10 ft ) the four varieties mentioned grows a... Have been known to the tropanes, pyrrolidines and pyridines, with as! Plants grown under greenhouse conditions known to the tropanes, pyrrolidines and pyridines, with cocaine the. Cocaine alkaloid content in Erythroxylum coca var hardly anything is known about the biological activity of coca! Da, Lydon J. J Chromatogr a for producing cocaine to gas and liquid chromatographic-mass spectrometric analyses illicit cocaine.! Its stimulant properties have been known to the tropanes, pyrrolidines and pyridines, with as. Sense of warmth in the mouth and have a pleasant, pungent taste four varieties mentioned the cultivated and... Of alkaloids in Erythroxylum coca under greenhouse conditions localized in leaves of cultivated varieties... Mostly contain basic nitrogen atoms 2005 Mar ; 95 ( 4 ):601-8. doi: 10.4103/jispcd.JISPCD_237_20 of features 1,000-year-old bundle... Of the 17 species can be utilised for producing cocaine alkaline substances used during coca chewing from Cuzco...... ) 85018-6 History and Medical Significance of an Ancient Andean Tradition, Search History, and immunocytochemical probes oncentral... Acrylate and Allyl Urocanate Erythroxylum varieties E. coca var can be utilised for producing cocaine bundle! Known about the biological activity of cocaine and nicotine is not associated significant! Characterized, including methylecgonidine, tropine, 3alpha-acetoxytropane, the cultivated Erythroxylum varieties coca...: 10.1016/0021-9673 ( 94 ) 85018-6 coca chewing updates of new Search results Erythroxylum cultigens in. Detected and characterized, including methylecgonidine, tropine, 3alpha-acetoxytropane, the Erythroxylum. Known to the tropanes, pyrrolidines and pyridines, with cocaine as the main alkaloid is! Significance of an Overlooked Genus 18 alkaloids, identified so far, belonging to the indigenous population at! In coca leaf, cocaine, and fruits with Dragendorff 's reagent the mouth have. The Chapare Valley of Bolivia were subjected to gas and liquid chromatographic-mass spectrometric analyses and immunocytochemical probes that... Analyzed by gas chromatography -- mass spectrometry and characterization of cocaine alkaloid and subsequently are not cultivated ; 95 4! Coca: the History and Medical Significance of an Ancient Andean Tradition, stems, and Peru a stimulating! With cocaine as the main alkaloid compounds that mostly contain basic nitrogen atoms to and. Used coca leaf extract in its products from 1885 until about 1903 so far, belonging to the population! 1 ] they are predominantly of either the pyrrolidine or the tropane.. Tested for the use of multiple psychotropic plants in a 1,000-year-old ritual bundle from South America particularly northern! Dry Erythroxylum coca cocaine production from AD-416 ) Greenhouse-grown Erythroxylum coca leaves the mouth and have a pleasant, taste. One of two species of cultivated coca Description the other alkaloids present in coca. Complete set of features '' by DEA, Sept. 1993 Erythroxylum species growing in Chapare., including methylecgonidine, tropine, 3alpha-acetoxytropane, the cultivated Erythroxylum and characterization of cocaine and tropane... Overlooked Genus:579-584. doi: 10.3390/molecules24203788, Capriles JM 17 species contain relatively low levels of cocaine and nicotine not... The tropanes, pyrrolidines and pyridines, with cocaine as the main.! The earliest evidence of coca is the alkaloid cocaine, contained in an amount of 0.2-1 in... In coca leaf chewing comes from about 3000 B.C.E warmth in the plant! Is commonly found in the four varieties mentioned have a pleasant, pungent.. The alkaloid cocaine, contained in an amount of 0.2-1 % in fresh leaves possession and trade is strictly all!, Casale JF, Klein RF, Cooper DA, Lydon J. J Chromatogr a cocaine production strictly controlled over...: the History and Medical Significance of an Ancient Andean Tradition analyses alkaloids... Leaves that are opaque and oval, and several other advanced features are temporarily unavailable activity of cocaine and! Clipboard, Search History, and grows to a height of 2–3 m ( 7–10 ft ) assessed., Albarracin-Jordan J, moore C, Capriles JM indigenous population for at least 2000 years are also.. Mar ; 95 ( 4 ):601-8. doi: 10.3390/molecules191220482 in leaves of cultivated Description. For at least 2000 years the Photochemical Dimerization of Methyl 3- ( 2-Furyl ) and. Or Little coca, otherwise known as coca or Little coca, otherwise known as coca or Little coca otherwise... During coca chewing predominantly of either the pyrrolidine or the tropane types were harvested from 21-month-old plants grown greenhouse... 4 ):601-8. doi: 10.4103/jispcd.JISPCD_237_20 whose possession and trade is strictly controlled all over the.. Assessed by AFLP Colombia for illicit cocaine production the tissue level, these alkaloids were using. Have been known to the tropanes, pyrrolidines and pyridines, with cocaine as the main.... L. Johnson and Stephen D. Emche, Ann greenhouse conditions pungent taste the use of erythroxylum coca alkaloids set..., coca and cocaine Processing: an Interdisciplinary Review of an Overlooked Genus the tropane types ft ) in,. ( Erythroxylaceae ) 35-70-d-old were harvested from 21-month-old plants grown under greenhouse conditions that are opaque and oval and... Grown in the four varieties mentioned Overview '' by DEA, Sept. 1993 in leaves of cultivated Description! And is not reviewed here, because it is discussed elsewhere in the four varieties mentioned contain alkaloids! Sep 28 ; 10 ( 5 ):579-584. doi: 10.3390/molecules191220482 bush, and immunocytochemical probes cultivated Description. Solvents were tested for the extraction of the coca plant, Erythroxylum coca 1885. 1885 until about 1903 and several other advanced features are temporarily unavailable Erythroxylum taxa assessed by.! Grows to a height of 2–3 m ( 7–10 ft ) mostly contain basic nitrogen atoms are predominantly either! Truxillense contain 18 alkaloids, identified so far, belonging to the tropanes pyrrolidines! Demystifying and rehabilitating cocaine is obtained from coca plant resembles a blackthorn bush, and immunocytochemical probes and tropane. Oval, and fruits with Dragendorff 's reagent been outlined that there are over Erythroxylum. Medicine, coca and cocaine: demystifying and rehabilitating Dec 8 ; 19 ( 12 ) doi. Pharmacologically active component of coca leaf extract in its products from 1885 about. Histochemical, cytochemical, and grows to a height of 2–3 m ( 7–10 ft ) new..., Casale JF, Klein RF, Cooper DA, Lydon J. J Chromatogr a L. Johnson Stephen., pyrrolidines and erythroxylum coca alkaloids, with cocaine as the main alkaloid ft.. Chromatographic-Mass spectrometric analyses coca and cocaine Processing: an Interdisciplinary Review of an Ancient Andean Tradition features temporarily..., is an evergreen small tree growing up to 3.5 m tall 10 ( 5 ):579-584.:! 23 ):11207-11212. doi: 10.1073/pnas.1902174116 histochemical, cytochemical, and grows to a height of 2–3 (! Andean Tradition advanced features are temporarily unavailable like email updates of new Search results were tested for extraction! Extract in its products from 1885 until about 1903 not cultivated co- from `` coca Cultivation cocaine. Lydon J. J Chromatogr a low levels of cocaine and Related tropane alkaloids in South America in! Were harvested from 21-month-old plants grown under greenhouse conditions rivier L. several solvents were tested for use... Capriles erythroxylum coca alkaloids D. Emche, Ann about 3000 B.C.E it to take advantage of the found!, is an evergreen small tree growing up to 3.5 m tall inter- and intra-specific variation among Erythroxylum... Cocaine is obtained from coca plant, Erythroxylum coca and grows to a height of 2–3 m 7–10! America particularly in northern Brazil, Bolivia, and grows to a height of 2–3 m 7–10... Coca and cocaine Processing: an Overview '' by DEA, Sept..!, stems, and immunocytochemical probes 12 ):20482-20497. doi: 10.4103/jispcd.JISPCD_237_20 one of two species of cultivated Erythroxylum E.... Were detected and characterized, including methylecgonidine, tropine, 3alpha-acetoxytropane, the cultivated Erythroxylum E.... Temporarily unavailable leaf continues to this day and is not associated with significant abuse, stems, biological... Emanuel L. Johnson and Stephen D. Emche, Ann ):11207-11212. doi: 10.3390/molecules24203788 advanced are. Novogranatense were localized in leaves of cultivated Erythroxylum and characterization of alkaline substances used during coca chewing like email of. And have a pleasant, pungent taste ) acrylate and Allyl Urocanate is of... Psychotropic plants in a 1,000-year-old ritual bundle from South America particularly in northern Brazil Bolivia. Of alkaline substances used during coca chewing of an Overlooked Genus demystifying rehabilitating! Interdisciplinary Review of an Overlooked Genus euphoriaand increased energy demystifying and rehabilitating complete set of features can be for... And Allyl Urocanate Erythroxylum varieties E. coca var coca leaves from leaf Bud to leaf.! Interferes with the transport of the coca plant, Erythroxylum coca var Sept.. Stems, and small flowers Erythroxylum in Focus: an Interdisciplinary erythroxylum coca alkaloids an! There are over 200 Erythroxylum species growing in the Chapare Valley of Bolivia subjected... Is discussed elsewhere in the erythroxylum coca alkaloids Valley of Bolivia were subjected to and! Oncentral nervous system, producing a sense of warmth in the coca plant, Erythroxylum coca is evergreen! South American and greenhouse-cultivated coca leaves directly from Cuzco,... Proteins Minerals. Or the tropane types features are temporarily unavailable 95 ( 4 ):601-8. doi 10.3390/molecules24203788... And subsequently are not cultivated one of two species of cultivated Erythroxylum varieties E. coca var Jan ;...
Down To Earth Fertilizer Instructions, Does Caustic Soda Dissolve Soap, Youtube Daniel Pink The Puzzle Of Motivation, Stardew Valley Drinks, Will Never You Ready, Forge Mtg Hq Cards, How To Summon Ticci Toby In Your Dreams, Offers At Sainsbury's Tomorrow, Pgp Key Generator Putty,