984:
961:
346:
233:
586:
2947:
vascular congestion and inflammation. Morbidity from its abuse is significant. The gastrointestinal tract sustains the brunt of toxicity, resulting in fatal hemorrhages. Renal toxicity is a result of its renal excretion, which may lead to acute tubular necrosis. Cardiac effects are most likely due to hemorrhagic shock, but they also can be due to myofibril degeneration, mitochondrial swelling, and pericardial and subendocardial hemorrhages.
1136:
581:
1227:
729:
29:
38:
1645:
806:
734:
733:
2946:
Cantharidin ("Spanish fly") is a chemical with vesicant properties derived from blister beetles, which has been used for millennia as a sexual stimulant by both sexes. Its mode of action is by inhibition of phosphodiesterase and protein phosphatase activity and stimulation of ÎČ-receptors, inducing
2804:
While most commonly available preparations of
Spanish fly contain cantharidin in negligible amounts, if at all, the chemical is available illicitly in concentrations capable of causing severe toxicity. Symptoms of cantharidin poisoning include burning of the mouth, dysphagia, nausea, hematemesis,
1572:
As a blister agent, cantharidin has the potential to cause adverse effects when used medically; for this reason, it has been included in a list of "problem drugs" used by dermatologists and emergency personnel. However, this references unregulated sources of cantharidin. In July 2023, the US FDA
1318:
Cantharides were in widespread use among the upper classes in France in the 1600s, despite being a banned substance. Police searches in connection with a rash of poisonings around 1680 turned up many stashes of "bluish flies", which were known to be used in the preparation of aphrodisiac
732:
1071:
Poisoning from cantharidin is a significant veterinary concern, especially in horses, but it can also be poisonous to humans if taken internally (where the source is usually experimental self-exposure). Externally, cantharidin is a potent
1739:
in animal models. In addition to topical medical applications, cantharidin and its analogues may have activity against cancer cells. Laboratory studies with cultured tumor cells suggest that this activity may be the result of
1548:
bird species, are not immune to the toxicity of cantharidin; they become intoxicated after ingesting blister beetles. However, cantharidin has activity also against parasites that infect them. Great bustards may eat toxic
1068:). In its natural form, cantharidin is secreted by the male blister beetle, and given to the female as a copulatory gift during mating. Afterwards, the female beetle covers her eggs with it as a defense against predators.
594:
561:
1625:
The extreme toxicity of cantharidin makes any use as an aphrodisiac highly dangerous. As a result, it is illegal to sell (or use) cantharidin or preparations containing it without a prescription in many countries.
1451:
of the coating of the eggs of the blister beetle, and additionally established that cantharidin had toxic properties comparable in degree to those of the most virulent poisons known in the 19th century, such as
2337:
2805:
gross hematuria, and dysuria. Mucosal erosion and hemorrhage is seen in the upper gastrointestinal (GI) tract. Renal dysfunction is common and related to acute tubular necrosis and glomerular destruction.
1311:
sprinkled a cantharid powder on food she served to him, after which the man experienced "violent priapism" and anal bleeding, of which he later died. Paré also cites the case of a priest who died of
3206:
Zhang C, Peng Y, Wang F, Tan X, Liu N, Fan S, et al. (December 2010). "A synthetic cantharidin analog for the enhancement of doxorubicin suppression of stem cell-derived aggressive sarcoma".
672:
1897:
3292:"Cantharidin, a potent and selective PP2A inhibitor, induces an oxidative stress-independent growth inhibition of pancreatic cancer cells through G2/M cell-cycle arrest and apoptosis"
2145:
1360:-flavored pastilles laced with Spanish fly to two prostitutes at a pair of orgies in 1772, poisoning and nearly killing them. He was sentenced to death for that (and for the crime of
2855:
475:
2038:
Bravo C, Mas-Peinado P, Bautista LM, Blanco G, Alonso JC, GarcĂa-ParĂs M (2017). "Cantharidin is conserved across phylogeographic lineages and present in both morphs of
Iberian
819:
138:
1531:, e.g., a single flake (4â5 in. section) may have several hundred insects, or none at all. Horses are very sensitive to the cantharidin produced by beetle infestations: the
1853:
1820:
2334:
1591:
is around 0.5 mg/kg, with a dose of as little as 10 mg being potentially fatal. Ingesting cantharidin can initially cause severe damage to the lining of the
735:
3159:"Norcantharidin-induced apoptosis is via the extracellular signal-regulated kinase and c-Jun-NH2-terminal kinase signaling pathways in human hepatoma HepG2 cells"
3000:
Bertaux B, Prost C, Heslan M, Dubertret L (February 1988). "Cantharide acantholysis: endogenous protease activation leading to desmosomal plaque dissolution".
3408:
2593:
Alonso JC, Magaña M, PalacĂn C, MartĂn CA (2010). "Correlates of male mating success in great bustard leks: the effects of age, weight, and display effort".
385:
1538:
for horses is roughly 1 mg/kg of the horse's body weight. Horses may be accidentally poisoned when fed bales of fodder with blister beetles in them.
1715:
VP-102, an experimental drug-device combination that includes cantharidin delivered via a single-use applicator, is being studied for the treatment of
668:
3368:
3114:
Ratcliffe NA, Mello CB, Garcia ES, Butt TM, Azambuja P (October 2011). "Insect natural products and processes: new treatments for human disease".
2011:
Capinera JL, Gardner DR, Stermitz FR (1985). "Cantharidin Levels in
Blister Beetles (Coleoptera: Meloidae) Associated with Alfalfa in Colorado".
1860:
2695:
SĂĄnchez-Barbudo IS, Camarero PR, GarcĂa-Montijano M, Mateo R (January 2012). "Possible cantharidin poisoning of a great bustard (Otis tarda)".
1285:, to entice members of the imperial family or dinner guests to commit sexual indiscretions (thus, providing her information to hold over them).
1088:
1080:. Properly dosed and applied, the same properties have also been used therapeutically, for instance, for treatment of skin conditions, such as
1519:
species (striped blister beetles) in the U.S. southwestâwhere the concentrations of the agent in each can vary substantially. Beetles feed on
2517:
2303:
A New Method of Curing the Small-pox ... with a
Specimen of Miscellaneous Observations on Medical Subjects; from the Latin ... by a Physician
2254:
2176:
2120:
1946:
1915:
1214:
have higher level of cantharidin per beetle: 64.22âŻÂ±âŻ51.28 mg/g (dry weight) and 9.10âŻÂ±âŻ12.64 mg/g (d. w.). Cantharidin content in
2571:
2137:
1440:. This was one of the first historical instances of the identification and extraction of a simple active principle from a complex medicine.
1258:, possibly because their physical effects were perceived to mimic those of sexual arousal, and because they can cause prolonged erection or
2307:
1511:
species from cantharidin is a significant veterinary concern, especially in horses; species infesting feedstocks depend on regionâe.g.,
2847:
1841:
2544:
2363:
1909:
750:
757:
360:
3044:"Verrica Pharmaceuticals Announces Extension of FDA Review Period of its NDA for VP-102 for the Treatment of Molluscum Contagiosum"
2740:
Heneberg P (2016). "On Otis tarda and
Marquis de Sade: what motivates male Great Bustards to consume Blister Beetles (Meloidae)?".
3373:
1812:
3378:
910:
861:
500:
3383:
542:
2480:
3051:
1338:
1095:, and is subject to strict reporting requirements by facilities that produce, store, or use it in significant quantities.
656:
2778:
Karras DJ, Farrell SE, Harrigan RA, Henretig FM, Gealt L (September 1996). "Poisoning from "Spanish fly" (cantharidin)".
826:
3413:
1289:
660:
634:
303:
2434:
880:
3398:
1858:"40 C.F.R.: Appendix A to Part 355âThe List of Extremely Hazardous Substances and Their Threshold Planning Quantities"
940:
324:
700:
585:
1379:
1375:
1337:
circles during the 1700s in France. They were multicolored tablets nicknamed "pastilles de
Richelieu," after the
240:
1964:"The Potential Organ Involved in Cantharidin Biosynthesis in Epicauta chinensis Laporte (Coleoptera: Meloidae)"
514:
692:
743:
688:
3393:
1736:
891:
676:
487:
979:
228:
1592:
1121:
1326:(known as "La Voisin," c. 1640â1680) was recorded in the 1670s as having prepared a love charm made from
1716:
1574:
1483:
1164:
1081:
1049:
608:
580:
573:
190:
1183:
The level of cantharidin in blister beetles can be quite variable. Among blister beetles of the genus
3403:
3123:
2649:
1857:
1210:
1160:
50:
1842:
https://www.fda.gov/drugs/news-events-human-drugs/fda-approves-first-treatment-molluscum-contagiosum
2197:
1545:
1394:
956:
648:
341:
104:
1116:
with solubility in various organic solvents, but only slight solubility in water. Its skeleton is
3331:
3272:
3025:
2937:
2757:
2618:
1585:
1532:
1342:
640:
150:
2567:
652:
3323:
3264:
3223:
3188:
3139:
3096:
3017:
2982:
2929:
2894:
2829:
2795:
2722:
2677:
2540:
2513:
2446:
2415:
2359:
2250:
2172:
2116:
2112:
2106:
1993:
1942:
1905:
1773:
1620:
1433:
1428:
1327:
1251:
1234:
1065:
925:
851:
526:
2301:
210:
3313:
3303:
3254:
3215:
3178:
3170:
3131:
3086:
3009:
2972:
2921:
2886:
2787:
2749:
2712:
2704:
2667:
2657:
2610:
2602:
2509:
2503:
2407:
2059:
2051:
2020:
1983:
1975:
1684:
1659:
1444:
1426:. Robiquet isolated cantharidin as the active ingredient in pharmacological preparations of
1296:
996:
408:
3352:
1135:
680:
312:
3388:
2341:
1864:
1788:
1419:
1353:
1282:
1218:
is also higher in males (80.9âŻÂ±âŻ106.5 ÎŒg/g) than in females (20.0âŻÂ±âŻ41.5 ÎŒg/g).
1113:
664:
2411:
2201:
369:
InChI=1S/C10H12O4/c1-9-5-3-4-6(13-5)10(9,2)8(12)14-7(9)11/h5-6H,3-4H2,1-2H3/t5-,6+,9-,10+
3318:
3291:
3127:
2653:
1658:
Please expand the section to include this information. Further details may exist on the
1226:
1163:
indicate that the biosynthetic process is more complicated, and not a simple product of
983:
960:
345:
232:
170:
114:
3219:
3183:
3158:
3013:
2672:
2637:
1988:
1963:
1596:
1550:
1437:
1300:
1247:
1045:
797:
2791:
1699:, cellular structures involved in cell-to-cell adhesion, leading to detachment of the
3362:
3308:
2890:
2244:
1692:
1541:
1448:
1304:
1139:
Biosynthesis from farnesolââ âââ bonds to be formed and major atoms to be added are in
1092:
1077:
972:
459:
221:
3335:
3276:
3029:
2941:
2761:
2476:
1867:(PDF) (1 July 2008 ed.). U.S. Government Printing Office. Retrieved 29 October 2011.
1707:), and ultimately results in blistering of the skin. Lesions heal without scarring.
1447:. He demonstrated that it was the active principle responsible for the aggressively
708:
2622:
1784:
1768:
1724:
1704:
1315:
after swallowing a dose of cantharides, which he intended to fortify his sex drive.
1152:
644:
3091:
3074:
2708:
1307:
and a cantharid extract. This is perhaps the same man of whom Paré relates that a
2977:
2960:
2912:
Sandroni P (October 2001). "Aphrodisiacs past and present: a historical review".
2662:
2638:"Males of a strongly polygynous species consume more poisonous food than females"
2534:
1703:
that hold cells together. The process leads to the loss of cellular connections (
1405:
of cantharidin as an effective preventative and treatment for smallpox, decrying
1299:(1510â1590) described a case in 1572 of a man suffering from "the most frightful
292:
2055:
1780:
1523:, and occasionally move into crop fields used to produce livestock feeds (e.g.,
1491:
1406:
1255:
1205:
contains 4.8 mg per beetle; males also contain higher levels than females.
1168:
1061:
783:
626:
3135:
3075:"Leishmania major: in vitro and in vivo anti-leishmanial effect of cantharidin"
3043:
1389:
Preparations of dried blister beetles were at one time used as a treatment for
696:
2753:
2606:
1700:
1453:
1398:
1215:
1143:; while bonds to be broken and atoms/structural segments to be removed are in
1023:
436:
201:
622:
3047:
2454:
2024:
1979:
1696:
1680:
1604:
1581:
1573:
approved a topical formulation of cantharidin (Ycanth) for the treatment of
1334:
1333:
Aphrodisiac sweets presumably laced with cantharides were circulated within
1323:
1312:
1308:
1175:(15-carbon) precursor from which certain carbon segments are later excised.
1117:
1041:
839:
37:
28:
3327:
3268:
3227:
3192:
3174:
3143:
3100:
2986:
2933:
2898:
2726:
2681:
2450:
2419:
1997:
1644:
3021:
2799:
2398:
Epstein WL, Kligman AM (May 1958). "Treatment of warts with cantharidin".
1352:
The French writer
Donatien Alphonse Françoisââ âââ notoriously known as the
2833:
1762:
1608:
1528:
1418:
Cantharidin was first isolated as a chemically pure substance in 1810 by
1402:
1390:
1346:
1259:
1190:
1185:
1172:
1156:
1129:
1073:
875:
756:
749:
742:
715:
2717:
2064:
2925:
2614:
1688:
1524:
1495:
1478:
1466:
1357:
1274:
898:
449:
279:
241:
3259:
3242:
1341:, a notorious libertine (not to be confused with his great-uncle, the
1120:, formally, a tricyclo-decane skeleton. Its functionalities include a
618:
1474:
1383:
1361:
1057:
181:
2961:"Cantharidin revisited: a blistering defense of an ancient medicine"
1735:
Cantharidin appears to have some effect in the topical treatment of
1443:
Robiquet found cantharidin to be an odorless and colorless solid at
1124:(âCOâOâCOâ) substructure in one of its rings, as well as a bridging
796:
Except where otherwise noted, data are given for materials in their
3290:
Li W, Xie L, Chen Z, Zhu Y, Sun Y, Miao Y, et al. (May 2010).
267:
2636:
Bravo C, Bautista LM, GarcĂa-ParĂs M, Blanco G, Alonso JC (2014).
1600:
1555:
1423:
1278:
1225:
1155:
of cantharidin is unknown. Its framework formally consists of two
1134:
1125:
1053:
614:
161:
137:
127:
1741:
1720:
1520:
1470:
704:
258:
919:
870:
520:
1898:"Overview of Cantharidin Poisoning (Blister Beetle Poisoning)"
1638:
3157:
Chen YN, Cheng CC, Chen JC, Tsauer W, Hsu SL (October 2003).
1277:
relates that a cantharid preparation was used by the empress
509:
945:
684:
329:
2274:. Cambridge, MA, USA: Harvard University Press. p. 58.
1527:), where they are found to cluster and find their way into
1679:
Topical cantharidin is absorbed by the lipid membranes of
1382:) (c. 1540â1610) reported the use of blister beetles as a
1269:
Examples of such use found in historical sources include:
727:
2848:"FDA approves first treatment for molluscum contagiosum"
2536:
Veterinary
Clinical Procedures in Large Animal Practices
2435:"Cutaneous warts: an evidence-based approach to therapy"
2379:
Robiquet PJ (1810). "Expériences sur les cantharides".
2095:, Springer Science & Business Media, 2012, pp.100ff
1167:
or related ten-carbon parent structure, as the seeming
1076:(blistering agent), exposure to which can cause severe
814:
71:)-3a,7a-Dimethylhexahydro-4,7-epoxybenzofuran-1,3-dione
2331:
The philosophy and mechanical principles of osteopathy
2289:. Universidad de Navarra - Iberoamericana - Vervuert.
2082:, Springer Science & Business Media, 2008. p.2010
2820:
Binder R (May 1979). "Malpractice--in dermatology".
2333:, 1892, chapter 12: "Smallpox". The 1902 edition is
3243:"The effect of cantharidins on leukemic stem cells"
2877:Shamloul R (January 2010). "Natural aphrodisiacs".
2246:
The beetle of
Aphrodite and other medical mysteries
1048:. Its main current use in pharmacology is treating
1022:
995:
990:
971:
939:
934:
909:
904:
890:
860:
850:
845:
2568:"Blister Beetle Poisoning / Cantharidin toxicosis"
1854:Emergency Planning and Community Right-to-Know Act
1603:damage. Symptoms of cantharidin poisoning include
1465:Diluted solutions of cantharidin can be used as a
1060:in large doses, and has been historically used as
2539:. Boston, MA, USA: Cengage Learning. p. 65.
2138:"When Sparks Fly: Aphrodisiacs and the Fruit Fly"
1292:(1050â1106) is said to have consumed cantharides.
1040:is an odorless, colorless fatty substance of the
1939:Secondary-Metabolite Biosynthesis and Metabolism
1904:. Kenilworth, NJ, USA: Merck Sharp & Dohme.
1515:(black blister beetle) in the U.S. midwest; and
291:
1695:in proteins. This causes the disintegration of
731:
113:
3241:Dorn DC, Kou CA, Png KJ, Moore MA (May 2009).
2959:Moed L, Shwayder TA, Chang MW (October 2001).
2815:
2813:
2773:
2771:
2231:Le Maréchal de Richelieu, un libertin fastueux
1330:mixed with dried mole's blood and bat's blood.
8:
2320:Cantharides referred to throughout the book.
1891:
1889:
1887:
1656:about toxicological mechanism when ingested.
1254:") have been used since ancient times as an
1044:class, which is secreted by many species of
879:
838:
2171:. W. W. Norton & Company. p. 170.
2780:The American Journal of Emergency Medicine
2287:Tesoros de la lengua castellana o española
2192:
2190:
2188:
1345:) who procured sexual encounters for King
1171:nature would suggest. Instead, there is a
982:
959:
344:
231:
209:
20:
3317:
3307:
3258:
3182:
3116:Insect Biochemistry and Molecular Biology
3090:
2976:
2716:
2671:
2661:
2356:Kompendium der TierÀrztlichen Homöopathie
2063:
2044:Zoological Journal of the Linnean Society
2042:blister beetles (Coleoptera, Meloidae)".
1987:
1941:. Springer Science & Business Media.
1559:to increase the sexual arousal of males.
1460:Other uses of the pharmacological isolate
1262:in men. These preparations were known as
311:
1937:Petroski RJ, McCormick SP, eds. (2012).
1112:, for beetle, is an odorless, colorless
3353:Cantharidin : origin and synthesis
2433:Bacelieri R, Johnson SM (August 2005).
2169:The Sexual Male: Problems and Solutions
1962:Jiang M, LĂŒ S, Zhang Y (January 2017).
1804:
1753:
1237:"), a beetle that secretes cantharidin.
955:
390:
365:
340:
2093:Aphrodisiacs: The Science and the Myth
1852:As defined in Section 302 of the U.S.
1356:(1740â1814)ââ âââ is said to have given
973:
837:
464:212 °C (414 °F; 485 K)
222:
2148:from the original on 29 November 2014
1517:E. occidentalis, temexia, and vittata
1364:), but was later reprieved on appeal.
372:Key: DHZBEENLJMYSHQ-YUMGAWCOSA-N
189:
169:
7:
2483:from the original on 18 October 2007
2412:10.1001/archderm.1958.01560050014003
2310:from the original on 14 January 2023
2080:Encyclopedia of Entomology, Volume 4
1303:" after taking a potion composed of
1266:, from the Greek word for "beetle".
3409:Heterocyclic compounds with 3 rings
2858:from the original on 11 August 2023
2595:Behavioral Ecology and Sociobiology
1823:from the original on 29 August 2023
282:
266:
3220:10.1016/j.biomaterials.2010.08.059
3014:10.1111/j.1365-2133.1988.tb01769.x
3002:The British Journal of Dermatology
2508:. Llewellyn Publications. p.
2243:Ford P, Howell, Michael M (1985).
2220:(London: Pan Books, 1969), p. 333.
1422:, a French chemist then living in
1056:topically. It is a burn agent and
14:
3054:from the original on 24 June 2021
2852:U.S. Food and Drug Administration
2574:from the original on 26 June 2010
2206:. Paris: A. Maloine. p. 498.
1900:. In Aiello SE, Moses MA (eds.).
1494:rituals, cantharides are used in
3309:10.1111/j.1349-7006.2010.01523.x
2891:10.1111/j.1743-6109.2009.01521.x
2479:. Merck Manuals. November 2005.
1643:
1087:Cantharidin is classified as an
1007:
804:
584:
579:
420:
36:
27:
3247:International Journal of Cancer
3163:British Journal of Pharmacology
1607:, abdominal pain, and (rarely)
1599:, and may also cause permanent
800:(at 25 °C , 100 kPa).
3369:Drugs not assigned an ATC code
3073:Ghaffarifar F (October 2010).
2879:The Journal of Sexual Medicine
2400:A.M.A. Archives of Dermatology
2285:Covarrubias-Horozco S (2006).
2013:Journal of Economic Entomology
1813:"Ycanth- cantharidin solution"
1151:The complete mechanism of the
1013:
1001:
543:Occupational safety and health
426:
414:
1:
3092:10.1016/j.exppara.2010.04.004
2792:10.1016/S0735-6757(96)90158-8
2709:10.1016/j.toxicon.2011.10.002
1376:Juan de Horozco y Covarrubias
1179:Distribution and availability
1089:extremely hazardous substance
2978:10.1001/archderm.137.10.1357
2663:10.1371/journal.pone.0111057
2533:Rockett J, Bosted S (2015).
2111:. Ballantine Books. p.
1273:The ancient Roman historian
1197:contains about 0.2 mg,
1108:Cantharidin, from the Greek
3355:at Lycée Faidherbe de Lille
2914:Clinical Autonomic Research
2502:Gonzalez-Wippler M (2002).
2272:The Marquis de Sade: A Life
1902:The Merck Veterinary Manual
1760:Including broadly in genus
1414:Pharmaco-chemical isolation
772:or concentration (LD, LC):
3430:
3136:10.1016/j.ibmb.2011.05.007
2249:. New York: Random House.
2136:Eplett L (13 March 2012).
1880:. CABI. 2011. p. 253.
1878:A Dictionary of Entomology
1618:
1386:as well as an aphrodisiac.
1201:contains 0.7 mg, and
1104:Structure and nomenclature
991:Chemical and physical data
3079:Experimental Parasitology
2754:10.1007/s10336-016-1369-8
2607:10.1007/s00265-010-0972-6
2439:American Family Physician
2056:10.1093/zoolinnean/zlw016
1968:Journal of Insect Science
1791:also produce cantharidin.
1683:, causing the release of
1477:, and to treat the small
1401:, recommended inhaling a
1122:carboxylic acid anhydride
794:
768:
560:
540:
535:
468:
401:
381:
356:
97:
77:
49:
44:
35:
26:
1863:25 February 2012 at the
1615:Risks of aphrodisiac use
1242:Aphrodisiac preparations
635:Precautionary statements
393:O=C2OC(1(C)3CC(O3)12C)=O
3374:Terpenes and terpenoids
2965:Archives of Dermatology
2477:"Molluscum contagiosum"
1856:(42 U.S.C. 11002). See
1737:cutaneous leishmaniasis
1246:Preparations made from
1084:infection of the skin.
790:0.03â0.5 mg/kg (human)
3379:Phosphatase inhibitors
3175:10.1038/sj.bjp.0705461
2742:Journal of Ornithology
2505:SanterĂa: The Religion
2233:(Paris, Perrin, 1971).
1654:is missing information
1513:Epicauta pennsylvanica
1374:The Spanish clergyman
1238:
1148:
738:
3384:Carboxylic anhydrides
2329:Andrew Taylor Still,
2025:10.1093/jee/78.5.1052
1980:10.1093/jisesa/iex021
1781:False blister beetles
1717:molluscum contagiosum
1575:molluscum contagiosum
1484:molluscum contagiosum
1469:medication to remove
1449:blistering properties
1339:Maréchal de Richelieu
1322:The French sorceress
1229:
1165:geranyl pyrophosphate
1138:
1082:molluscum contagiosum
1050:molluscum contagiosum
737:
2340:14 July 2019 at the
2270:Schaeffer N (2000).
1563:Human medical issues
1369:Non-aphrodisiac uses
1211:Berberomeloe majalis
720:(fire diamond)
51:Preferred IUPAC name
3414:Oxygen heterocycles
3128:2011IBMB...41..747R
2654:2014PLoSO...9k1057B
2216:Richard Cavendish,
2203:RemĂšdes d'autrefois
2142:Scientific American
2091:Peter V. Taberner,
1918:on 22 December 2015
1896:Schmitz DG (2013).
1635:Mechanism of action
1609:prolonged erections
1395:Andrew Taylor Still
1393:. As late as 1892,
1324:Catherine Monvoisin
1295:The French surgeon
1288:The German emperor
842:
444: g·mol
151:Beilstein Reference
23:
3399:Insects in culture
2926:10.1007/BF02332975
2167:Milsten R (2000).
2108:Ancient Inventions
2078:John L. Capinera,
1711:Pharmaceutical use
1697:desmosomal plaques
1605:blood in the urine
1343:Cardinal Richelieu
1239:
1149:
827:Infobox references
739:
21:
3260:10.1002/ijc.24157
3214:(36): 9535â9543.
2971:(10): 1357â1360.
2885:(1 Pt 1): 39â49.
2601:(10): 1589â1600.
2519:978-1-56718-329-0
2381:Annales de Chimie
2354:Wolter H (1995).
2300:Closs JF (1767).
2256:978-0-394-54797-8
2178:978-0-393-32127-2
2122:978-0-345-40102-1
1948:978-0-306-44309-1
1775:Lytta vesicatoria
1772:, and in species
1677:
1676:
1621:Lytta vesicatoria
1503:Veterinary issues
1429:Lytta vesicatoria
1397:, the founder of
1231:Lytta vesicatoria
1035:
1034:
941:CompTox Dashboard
923:
873:
835:Chemical compound
833:
832:
609:Hazard statements
524:
512:
325:CompTox Dashboard
139:Interactive image
16:Chemical compound
3421:
3340:
3339:
3321:
3311:
3302:(5): 1226â1233.
3287:
3281:
3280:
3262:
3253:(9): 2186â2199.
3238:
3232:
3231:
3203:
3197:
3196:
3186:
3154:
3148:
3147:
3111:
3105:
3104:
3094:
3070:
3064:
3063:
3061:
3059:
3040:
3034:
3033:
2997:
2991:
2990:
2980:
2956:
2950:
2949:
2909:
2903:
2902:
2874:
2868:
2867:
2865:
2863:
2854:. 24 July 2023.
2844:
2838:
2837:
2817:
2808:
2807:
2775:
2766:
2765:
2748:(4): 1123â1125.
2737:
2731:
2730:
2720:
2692:
2686:
2685:
2675:
2665:
2633:
2627:
2626:
2590:
2584:
2583:
2581:
2579:
2564:
2558:
2557:
2555:
2553:
2530:
2524:
2523:
2499:
2493:
2492:
2490:
2488:
2473:
2467:
2466:
2464:
2462:
2453:. Archived from
2430:
2424:
2423:
2395:
2389:
2388:
2376:
2370:
2369:
2351:
2345:
2327:
2321:
2319:
2317:
2315:
2297:
2291:
2290:
2282:
2276:
2275:
2267:
2261:
2260:
2240:
2234:
2229:Jacques Levron,
2227:
2221:
2214:
2208:
2207:
2194:
2183:
2182:
2164:
2158:
2157:
2155:
2153:
2133:
2127:
2126:
2105:James P (1995).
2102:
2096:
2089:
2083:
2076:
2070:
2069:
2067:
2035:
2029:
2028:
2019:(5): 1052â1055.
2008:
2002:
2001:
1991:
1959:
1953:
1952:
1934:
1928:
1927:
1925:
1923:
1914:. Archived from
1893:
1882:
1881:
1874:
1868:
1850:
1844:
1839:
1833:
1832:
1830:
1828:
1819:. 25 July 2023.
1809:
1792:
1785:cardinal beetles
1758:
1685:serine proteases
1672:
1669:
1663:
1647:
1639:
1593:gastrointestinal
1445:room temperature
1436:", a species of
1195:E. pennsylvanica
1159:units. However,
1146:
1142:
1030:
1015:
1009:
1003:
986:
975:
964:
963:
949:
947:
921:
918:
883:
872:
869:
843:
841:
817:
811:
808:
807:
759:
752:
745:
730:
710:
706:
702:
698:
694:
690:
686:
682:
678:
674:
670:
666:
662:
658:
654:
650:
646:
642:
628:
624:
620:
616:
588:
583:
522:
519:
511:
508:
443:
428:
422:
416:
409:Chemical formula
349:
348:
333:
331:
315:
295:
284:
270:
243:
235:
224:
213:
193:
173:
141:
117:
40:
31:
24:
3429:
3428:
3424:
3423:
3422:
3420:
3419:
3418:
3359:
3358:
3349:
3344:
3343:
3289:
3288:
3284:
3240:
3239:
3235:
3205:
3204:
3200:
3156:
3155:
3151:
3122:(10): 747â769.
3113:
3112:
3108:
3072:
3071:
3067:
3057:
3055:
3050:. 28 May 2021.
3042:
3041:
3037:
2999:
2998:
2994:
2958:
2957:
2953:
2911:
2910:
2906:
2876:
2875:
2871:
2861:
2859:
2846:
2845:
2841:
2819:
2818:
2811:
2777:
2776:
2769:
2739:
2738:
2734:
2694:
2693:
2689:
2648:(10): e111057.
2635:
2634:
2630:
2592:
2591:
2587:
2577:
2575:
2566:
2565:
2561:
2551:
2549:
2547:
2532:
2531:
2527:
2520:
2501:
2500:
2496:
2486:
2484:
2475:
2474:
2470:
2460:
2458:
2432:
2431:
2427:
2397:
2396:
2392:
2378:
2377:
2373:
2366:
2353:
2352:
2348:
2342:Wayback Machine
2328:
2324:
2313:
2311:
2299:
2298:
2294:
2284:
2283:
2279:
2269:
2268:
2264:
2257:
2242:
2241:
2237:
2228:
2224:
2215:
2211:
2196:
2195:
2186:
2179:
2166:
2165:
2161:
2151:
2149:
2135:
2134:
2130:
2123:
2104:
2103:
2099:
2090:
2086:
2077:
2073:
2037:
2036:
2032:
2010:
2009:
2005:
1961:
1960:
1956:
1949:
1936:
1935:
1931:
1921:
1919:
1912:
1895:
1894:
1885:
1876:
1875:
1871:
1865:Wayback Machine
1851:
1847:
1840:
1836:
1826:
1824:
1811:
1810:
1806:
1801:
1796:
1795:
1789:soldier beetles
1759:
1755:
1750:
1733:
1713:
1691:that break the
1681:epidermal cells
1673:
1667:
1664:
1657:
1648:
1637:
1632:
1623:
1617:
1589:
1584:by humans, the
1570:
1565:
1551:blister beetles
1536:
1505:
1462:
1420:Pierre Robiquet
1416:
1371:
1354:Marquis de Sade
1283:Augustus Caesar
1250:(particularly "
1248:blister beetles
1244:
1224:
1181:
1161:feeding studies
1144:
1140:
1114:natural product
1106:
1101:
1046:blister beetles
1028:
1018:
1012:
1006:
967:
943:
930:
893:
886:
836:
829:
824:
823:
822: ?)
813:
809:
805:
801:
787:
781:
764:
763:
762:
761:
754:
747:
740:
736:
728:
637:
611:
597:
576:
553:
531:
492:
489:
478:
441:
431:
425:
419:
411:
397:
394:
389:
388:
377:
374:
373:
370:
364:
363:
352:
334:
327:
318:
298:
285:
273:
253:
216:
196:
176:
153:
144:
131:
120:
107:
93:
92:
73:
72:
17:
12:
11:
5:
3427:
3425:
3417:
3416:
3411:
3406:
3401:
3396:
3394:Blister agents
3391:
3386:
3381:
3376:
3371:
3361:
3360:
3357:
3356:
3348:
3347:External links
3345:
3342:
3341:
3296:Cancer Science
3282:
3233:
3198:
3169:(3): 461â470.
3149:
3106:
3085:(2): 126â129.
3065:
3035:
3008:(2): 157â165.
2992:
2951:
2920:(5): 303â307.
2904:
2869:
2839:
2828:(5): 663â666.
2809:
2786:(5): 478â483.
2767:
2732:
2703:(1): 100â103.
2687:
2628:
2585:
2559:
2546:978-1305537651
2545:
2525:
2518:
2494:
2468:
2457:on 9 July 2008
2445:(4): 647â652.
2425:
2406:(5): 508â511.
2390:
2371:
2365:978-3432978925
2364:
2346:
2335:available here
2322:
2292:
2277:
2262:
2255:
2235:
2222:
2218:The Black Arts
2209:
2184:
2177:
2159:
2128:
2121:
2097:
2084:
2071:
2050:(4): 790â804.
2030:
2003:
1954:
1947:
1929:
1911:978-0911910612
1910:
1883:
1869:
1845:
1834:
1803:
1802:
1800:
1797:
1794:
1793:
1752:
1751:
1749:
1746:
1732:
1729:
1712:
1709:
1675:
1674:
1668:September 2022
1651:
1649:
1642:
1636:
1633:
1631:
1628:
1619:Main article:
1616:
1613:
1597:urinary tracts
1587:
1569:
1566:
1564:
1561:
1542:Great bustards
1534:
1504:
1501:
1500:
1499:
1488:
1461:
1458:
1438:blister beetle
1415:
1412:
1411:
1410:
1387:
1370:
1367:
1366:
1365:
1350:
1331:
1320:
1316:
1293:
1286:
1243:
1240:
1223:
1220:
1180:
1177:
1105:
1102:
1100:
1097:
1078:chemical burns
1033:
1032:
1026:
1020:
1019:
1016:
1010:
1004:
999:
993:
992:
988:
987:
977:
969:
968:
966:
965:
952:
950:
937:
936:
932:
931:
929:
928:
915:
913:
907:
906:
902:
901:
896:
894:administration
888:
887:
885:
884:
866:
864:
858:
857:
856:Ycanth, others
854:
848:
847:
834:
831:
830:
825:
803:
802:
798:standard state
795:
792:
791:
788:
779:
777:
774:
773:
766:
765:
755:
748:
741:
726:
725:
724:
723:
721:
712:
711:
673:P305+P351+P338
638:
633:
630:
629:
612:
607:
604:
603:
598:
593:
590:
589:
577:
572:
569:
568:
558:
557:
554:
551:
548:
547:
538:
537:
533:
532:
530:
529:
517:
505:
503:
497:
496:
493:
490:administration
486:
483:
482:
479:
474:
471:
470:
466:
465:
462:
456:
455:
452:
446:
445:
439:
433:
432:
429:
423:
417:
412:
407:
404:
403:
399:
398:
396:
395:
392:
384:
383:
382:
379:
378:
376:
375:
371:
368:
367:
359:
358:
357:
354:
353:
351:
350:
337:
335:
323:
320:
319:
317:
316:
308:
306:
300:
299:
297:
296:
288:
286:
278:
275:
274:
272:
271:
263:
261:
255:
254:
252:
251:
247:
245:
237:
236:
226:
218:
217:
215:
214:
206:
204:
198:
197:
195:
194:
186:
184:
178:
177:
175:
174:
166:
164:
158:
157:
154:
149:
146:
145:
143:
142:
134:
132:
125:
122:
121:
119:
118:
110:
108:
103:
100:
99:
95:
94:
91:
90:
87:
84:
80:
79:
75:
74:
54:
53:
47:
46:
42:
41:
33:
32:
15:
13:
10:
9:
6:
4:
3:
2:
3426:
3415:
3412:
3410:
3407:
3405:
3402:
3400:
3397:
3395:
3392:
3390:
3387:
3385:
3382:
3380:
3377:
3375:
3372:
3370:
3367:
3366:
3364:
3354:
3351:
3350:
3346:
3337:
3333:
3329:
3325:
3320:
3315:
3310:
3305:
3301:
3297:
3293:
3286:
3283:
3278:
3274:
3270:
3266:
3261:
3256:
3252:
3248:
3244:
3237:
3234:
3229:
3225:
3221:
3217:
3213:
3209:
3202:
3199:
3194:
3190:
3185:
3180:
3176:
3172:
3168:
3164:
3160:
3153:
3150:
3145:
3141:
3137:
3133:
3129:
3125:
3121:
3117:
3110:
3107:
3102:
3098:
3093:
3088:
3084:
3080:
3076:
3069:
3066:
3053:
3049:
3045:
3039:
3036:
3031:
3027:
3023:
3019:
3015:
3011:
3007:
3003:
2996:
2993:
2988:
2984:
2979:
2974:
2970:
2966:
2962:
2955:
2952:
2948:
2943:
2939:
2935:
2931:
2927:
2923:
2919:
2915:
2908:
2905:
2900:
2896:
2892:
2888:
2884:
2880:
2873:
2870:
2857:
2853:
2849:
2843:
2840:
2835:
2831:
2827:
2823:
2816:
2814:
2810:
2806:
2801:
2797:
2793:
2789:
2785:
2781:
2774:
2772:
2768:
2763:
2759:
2755:
2751:
2747:
2743:
2736:
2733:
2728:
2724:
2719:
2714:
2710:
2706:
2702:
2698:
2691:
2688:
2683:
2679:
2674:
2669:
2664:
2659:
2655:
2651:
2647:
2643:
2639:
2632:
2629:
2624:
2620:
2616:
2612:
2608:
2604:
2600:
2596:
2589:
2586:
2573:
2569:
2563:
2560:
2548:
2542:
2538:
2537:
2529:
2526:
2521:
2515:
2511:
2507:
2506:
2498:
2495:
2482:
2478:
2472:
2469:
2456:
2452:
2448:
2444:
2440:
2436:
2429:
2426:
2421:
2417:
2413:
2409:
2405:
2401:
2394:
2391:
2386:
2382:
2375:
2372:
2367:
2361:
2357:
2350:
2347:
2343:
2339:
2336:
2332:
2326:
2323:
2309:
2305:
2304:
2296:
2293:
2288:
2281:
2278:
2273:
2266:
2263:
2258:
2252:
2248:
2247:
2239:
2236:
2232:
2226:
2223:
2219:
2213:
2210:
2205:
2204:
2199:
2193:
2191:
2189:
2185:
2180:
2174:
2170:
2163:
2160:
2147:
2143:
2139:
2132:
2129:
2124:
2118:
2114:
2110:
2109:
2101:
2098:
2094:
2088:
2085:
2081:
2075:
2072:
2066:
2061:
2057:
2053:
2049:
2045:
2041:
2034:
2031:
2026:
2022:
2018:
2014:
2007:
2004:
1999:
1995:
1990:
1985:
1981:
1977:
1973:
1969:
1965:
1958:
1955:
1950:
1944:
1940:
1933:
1930:
1917:
1913:
1907:
1903:
1899:
1892:
1890:
1888:
1884:
1879:
1873:
1870:
1866:
1862:
1859:
1855:
1849:
1846:
1843:
1838:
1835:
1822:
1818:
1814:
1808:
1805:
1798:
1790:
1786:
1782:
1778:
1777:(Spanish fly)
1776:
1771:
1770:
1765:
1764:
1757:
1754:
1747:
1745:
1743:
1738:
1731:Bioactivities
1730:
1728:
1726:
1725:genital warts
1722:
1718:
1710:
1708:
1706:
1702:
1701:tonofilaments
1698:
1694:
1693:peptide bonds
1690:
1686:
1682:
1671:
1661:
1655:
1652:This section
1650:
1646:
1641:
1640:
1634:
1629:
1627:
1622:
1614:
1612:
1610:
1606:
1602:
1598:
1594:
1590:
1583:
1578:
1576:
1568:General risks
1567:
1562:
1560:
1558:
1557:
1553:of the genus
1552:
1547:
1544:, a strongly
1543:
1539:
1537:
1530:
1526:
1522:
1518:
1514:
1510:
1507:Poisoning by
1502:
1497:
1493:
1489:
1486:
1485:
1480:
1476:
1472:
1468:
1464:
1463:
1459:
1457:
1455:
1450:
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3056:. Retrieved
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2459:. Retrieved
2455:the original
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2040:Berberomeloe
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2012:
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1938:
1932:
1920:. Retrieved
1916:the original
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1825:. Retrieved
1816:
1807:
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1769:Berberomeloe
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1744:inhibition.
1734:
1721:common warts
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1705:acantholysis
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1062:aphrodisiacs
1037:
1036:
911:Legal status
905:Legal status
862:License data
769:
716:
600:
562:
552:Main hazards
541:
501:Legal status
98:Identifiers
78:Other names
68:
64:
60:
56:
22:Cantharidin
18:
3404:Dermatoxins
2615:10261/76985
2578:31 December
2552:14 December
2152:18 November
1922:14 December
1434:Spanish fly
1407:vaccination
1328:Spanish fly
1264:cantharides
1256:aphrodisiac
1252:Spanish fly
1235:Spanish fly
1199:E. maculata
1169:monoterpene
1066:Spanish fly
1038:Cantharidin
1031: g·mol
980:100.000.240
935:Identifiers
881:Cantharidin
852:Trade names
840:Cantharidin
784:median dose
770:Lethal dose
595:Signal word
546:(OHS/OSH):
402:Properties
229:100.000.240
191:ChEMBL48449
171:CHEBI:64213
86:Spanish fly
83:Cantharidin
3363:Categories
2487:21 October
2461:2 December
2387:: 302â322.
1799:References
1546:polygynous
1454:strychnine
1432:, a.k.a. "
1399:osteopathy
1301:satyriasis
1281:, wife of
1216:haemolymph
1024:Molar mass
574:Pictograms
454:1.41 g/cm
437:Molar mass
313:IGL471WQ8P
202:ChemSpider
126:3D model (
105:CAS Number
3048:drugs.com
2306:. Hawes.
2198:CabanĂšs A
1974:(2): 52.
1827:28 August
1660:talk page
1529:baled hay
1335:libertine
1313:hematuria
1309:courtesan
1208:Males of
1118:tricyclic
1110:kantharis
1099:Chemistry
1058:poisonous
1042:terpenoid
892:Routes of
701:P403+P233
693:P337+P313
689:P332+P313
669:P304+P340
665:P302+P352
661:P301+P310
565:labelling
488:Routes of
250:200-263-3
242:EC Number
3336:24345174
3328:20331621
3319:11158714
3277:38088568
3269:19123473
3228:20875681
3193:12970086
3144:21658450
3101:20435039
3052:Archived
3030:45714898
2987:11594862
2942:32348540
2934:11758796
2899:19796015
2862:6 August
2856:Archived
2762:17325635
2727:22001622
2682:25337911
2642:PLOS ONE
2572:Archived
2481:Archived
2451:16127954
2420:13519856
2358:. Enke.
2338:Archived
2314:15 April
2308:Archived
2200:(1910).
2146:Archived
1998:28423415
1861:Archived
1821:Archived
1817:DailyMed
1766:, genus
1763:Epicauta
1630:Research
1582:ingested
1509:Epicauta
1492:SanterĂa
1403:tincture
1391:smallpox
1347:Louis XV
1319:potions.
1290:Henry IV
1260:priapism
1233:(a.k.a "
1191:Colorado
1186:Epicauta
1173:farnesol
1157:isoprene
1130:bicyclic
1074:vesicant
876:DailyMed
717:NFPA 704
536:Hazards
495:Topical
476:ATC code
3184:1574052
3124:Bibcode
3058:24 June
3022:3279999
2800:8765116
2697:Toxicon
2673:4206510
2650:Bibcode
2623:8741416
1989:5633858
1689:enzymes
1525:alfalfa
1496:incense
1479:papules
1475:tattoos
1467:topical
1358:aniseed
1305:nettles
1275:Tacitus
1222:History
1128:in its
1091:in the
1029:196.202
997:Formula
899:Topical
878::
820:what is
818: (
515:Class A
513::
450:Density
442:196.202
280:PubChem
211:2297293
115:56-25-7
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926:â-only
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812:
601:Danger
527:â-only
525:
386:SMILES
268:C16778
182:ChEMBL
156:85302
89:Ycanth
45:Names
3332:S2CID
3273:S2CID
3026:S2CID
2938:S2CID
2822:Cutis
2758:S2CID
2619:S2CID
1748:Notes
1601:renal
1580:When
1556:Meloe
1521:weeds
1471:warts
1424:Paris
1279:Livia
1126:ether
1054:warts
481:None
361:InChI
162:ChEBI
128:JSmol
3324:PMID
3265:PMID
3224:PMID
3189:PMID
3140:PMID
3097:PMID
3060:2021
3018:PMID
2983:PMID
2930:PMID
2895:PMID
2864:2023
2830:PMID
2796:PMID
2723:PMID
2678:PMID
2580:2010
2554:2015
2541:ISBN
2514:ISBN
2489:2007
2463:2012
2447:PMID
2416:PMID
2360:ISBN
2316:2017
2251:ISBN
2173:ISBN
2154:2014
2117:ISBN
1994:PMID
1943:ISBN
1924:2015
1906:ISBN
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645:P264
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627:H335
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615:H300
304:UNII
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2603:doi
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2113:177
2060:hdl
2052:doi
2048:180
2021:doi
1984:PMC
1976:doi
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