Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Allopumiliotoxin 267A: Difference between pages

| Verifiedfields = changed

| verifiedrevid = 477314460

|ImageFile=Allopumiliotoxin 267A.svg

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

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

| 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

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

| Appearance=

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| MeltingPt=

| BoilingPt=

| Solubility=

| MainHazards=Highly toxic

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| AutoignitionPt =

'''Allopumiliotoxin 267A''' is a toxin found in the skin of several [[poison frog]]s of the family ''[[Dendrobates]]''.<ref>{{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}}</ref> It is a member of the class of compounds known as [[allopumiliotoxin]]s. The frogs produce the toxin by modifying the original version, [[pumiliotoxin 251D]].<ref>{{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}}</ref> 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.<ref>{{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}}</ref><ref>{{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. }}</ref><ref>{{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 | url =https://figshare.com/articles/Nickel-Catalyzed_Preparation_of_Bicyclic_Heterocycles_Total_Synthesis_of_-Allopumiliotoxin_267A_-Allopumiliotoxin_339A_and_-Allopumiliotoxin_339B/3629484 }}</ref><ref>{{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 }}</ref>

== See also ==

* [[Pumiliotoxin]]

* [[Allopumiliotoxin]]

== References ==

{{reflist}}

{{Poison frog alkaloids}}

[[Category:Amphibian toxins]]

[[Category:Alkaloids]]

[[Category:Ion channel toxins]]

[[Category:Vicinal diols]]