:Allopumiliotoxin 267A

{{chembox

| Verifiedfields = changed

| verifiedrevid = 477314460

|ImageFile=Allopumiliotoxin 267A.svg

|ImageSize=240

|PIN=(6E,7R,8R,8aS)-8-Methyl-6-[(2R)-2-methylhexylidene]octahydroindolizine-7,8-diol

|OtherNames=

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4580699

| InChI = 1/C16H29NO2/c1-4-5-7-12(2)10-13-11-17-9-6-8-14(17)16(3,19)15(13)18/h10,12,14-15,18-19H,4-9,11H2,1-3H3/b13-10+/t12-,14+,15-,16-/m1/s1

| InChIKey = LWXKAVPXEDNHLL-VRUXTKGDBX

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C16H29NO2/c1-4-5-7-12(2)10-13-11-17-9-6-8-14(17)16(3,19)15(13)18/h10,12,14-15,18-19H,4-9,11H2,1-3H3/b13-10+/t12-,14+,15-,16-/m1/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = LWXKAVPXEDNHLL-VRUXTKGDSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo= 73376-38-2

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = TEP57TLJ38

| PubChem = 5470308

| SMILES = O[C@@H]1C(=C\[C@H](C)CCCC)\CN2[C@H]([C@]1(O)C)CCC2

}}

|Section2={{Chembox Properties

| C=16 | H=29 | N=1 | O=2

| Appearance=

| Density=

| MeltingPt=

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|Section3={{Chembox Hazards

| MainHazards=Highly toxic

| FlashPt=

| AutoignitionPt =

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Allopumiliotoxin 267A is a toxin found in the skin of several poison frogs of the family Dendrobates.{{Cite journal | pmid = 3236011| year = 1988| last1 = Edwards| first1 = M. W.| title = Alkaloids from a Panamanian poison frog, Dendrobates speciosus: Identification of pumiliotoxin-A and allopumiliotoxin class alkaloids, 3,5-disubstituted indolizidines, 5-substituted 8-methylindolizidines, and a 2-methyl-6-nonyl-4-hydroxypiperidine| journal = Journal of Natural Products| volume = 51| issue = 6| pages = 1188–97| last2 = Daly| first2 = J. W.| last3 = Myers| first3 = C. W.| doi = 10.1021/np50060a023}} It is a member of the class of compounds known as allopumiliotoxins. The frogs produce the toxin by modifying the original version, pumiliotoxin 251D.{{Cite journal | pmid = 12960405| pmc = 196932| year = 2003| last1 = Daly| first1 = J. W.| title = Evidence for an enantioselective pumiliotoxin 7-hydroxylase in dendrobatid poison frogs of the genus Dendrobates| journal = Proceedings of the National Academy of Sciences of the United States of America| volume = 100| issue = 19| pages = 11092–7| last2 = Garraffo| first2 = H. M.| last3 = Spande| first3 = T. F.| last4 = Clark| first4 = V. C.| last5 = Ma| first5 = J.| last6 = Ziffer| first6 = H.| last7 = Cover Jr| first7 = J. F.| doi = 10.1073/pnas.1834430100| bibcode = 2003PNAS..10011092D| doi-access = free}} It has been tested on mice and found to be five times more potent than the former version. It has been produced synthetically through a variety of different routes.{{Cite journal | pmid = 11428041| year = 2001| last1 = Comins| first1 = D. L.| title = Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates: A concise asymmetric synthesis of (+)-allopumiliotoxin 267A| journal = Organic Letters| volume = 3| issue = 3| pages = 469–71| last2 = Huang| first2 = S.| last3 = McArdle| first3 = C. L.| last4 = Ingalls| first4 = C. L.| doi = 10.1021/ol0069709}}{{cite journal | doi = 10.1021/cr950021p | pmid = 11848762 | title = Total Syntheses of Pumiliotoxin a and Allopumiliotoxin Alkaloids. Interplay of Pharmacologically Active Natural Products and New Synthetic Methods and Strategies | journal = Chemical Reviews | volume = 96 | issue = 1 | pages = 505–522 | year = 1996 | last1 = Franklin | first1 = Alison S. | last2 = Overman | first2 = Larry E. }}{{cite journal | doi =10.1021/ja001440t | title =Nickel-Catalyzed Preparation of Bicyclic Heterocycles: Total Synthesis of (+)-Allopumiliotoxin 267A, (+)-Allopumiliotoxin 339A, and (+)-Allopumiliotoxin 339B | journal =Journal of the American Chemical Society | volume =122 | issue =29 | pages =6950–6954 | year =2000 | last1 =Tang | first1 =Xiao-Qing | last2 =Montgomery | first2 =John | bibcode =2000JAChS.122.6950T | url =https://figshare.com/articles/Nickel-Catalyzed_Preparation_of_Bicyclic_Heterocycles_Total_Synthesis_of_-Allopumiliotoxin_267A_-Allopumiliotoxin_339A_and_-Allopumiliotoxin_339B/3629484 | url-access =subscription }}{{cite journal | doi =10.1021/ja00077a044 | title =Highly stereoselective total syntheses of (+)-allopumiliotoxins 267A and 339A via intramolecular nickel(II)/Chromium(II)-mediated cyclization | journal =Journal of the American Chemical Society | volume =115 | issue =24 | pages =11393–11409 | year =1993 | last1 =Aoyagi | first1 =Sakae | last2 =Wang | first2 =Tzu Chueh | last3 =Kibayashi | first3 =Chihiro | bibcode =1993JAChS.11511393A }}