Abstract Plants in the genus Galbulimima (GB) produce a series of neuroactive alkaloids that have proven impractical to obtain and study by isolation or chemical synthesis. The role of GB extracts in traditional Papuan medicine and ritual suggests that one or more alkaloids reach the brain by ingestion; identification of potent muscarinic and opioid receptor antagonists among the GB alkaloids...
) that has a unique therapeutic potential across multiple indications, including opioid dependence, substance use disorders, depression, anxiety, posttraumatic stress disorder (PTSD), and traumatic brain injury (TBI). We systematically examined the effects of ibogaine, its main metabolite noribogaine, and a series of iboga analogs at monoamine neurotransmitter transporters, some of which have...
A light-induced cyclization via a radical spin-center shift process that results in the direct functionalization of the indole ring at the C4-position is developed into a practical method for the synthesis of medicinally active, ring-constrained tryptamine analogs. Amino acids were coupled to tryptamine and irradiated with UV light to produce a library of lactams bridging the C3- and...
The serotonergic transmitter system plays fundamental roles in the nervous system in neurotransmission, synaptic plasticity, pathological processes, and therapeutic effects of antidepressants and psychedelics, as well as in the gastrointestinal and circulatory systems. We introduce a novel small molecule fluorescent agent, termed SERTlight, that specifically labels serotonergic neuronal cell...
(-)-Ibogaine and (-)-voacangine are plant derived psychoactives that show promise as treatments for opioid addiction. However, these compounds are produced by hard to source plants, making these chemicals difficult for broad-scale use. Here we report the complete biosynthesis of (-)-voacangine, and de-esterified voacangine, which is converted to (-)-ibogaine by heating, enabling biocatalytic...
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTPhotoelectron spectra of psychotropic drugs. 1. Phenethylamines, tryptamines, and LSDL. N. Domelsmith, Linda L. Munchausen, and K. N. HoukCite this: J. Am. Chem. Soc. 1977, 99, 13, 4311–4321Publication Date (Print):June 1, 1977Publication History Published online1 May 2002Published inissue 1 June...
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTPhotocyclizations of pharmacodynamic amines. V. Unusual rearrangements of the mescaline skeletonOsamu Yonemitsu, Hideo Nakai, Yuichi Kanaoka, Isabella L. Karle, and Bernhard WitkopCite this: J. Am. Chem. Soc. 1970, 92, 19, 5691–5700Publication Date (Print):September 1, 1970Publication History Published online1 May 2002Published inissue 1 September...
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTPhotocyclizations of pharmacodynamic amines. III. Three-dimensional structure of 7-hydroxy-1,9,10-trimethoxy-4-azabicyclo[5.2.2]undeca-8,10-dien-3-one from mescalineOsamu Yonemitsu, H. Nakai, Yuichi Kanaoka, Isabella L. Karle, and Bernhard WitkopCite this: J. Am. Chem. Soc. 1969, 91, 16, 4591–4593Publication Date (Print):July 1, 1969Publication...
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTBiosynthesis of the Peyote Alkaloids. The Incorporation of Tyrosine-2-C14 into Mescaline and Anhalonidine1Edward LeeteCite this: J. Am. Chem. Soc. 1966, 88, 18, 4218–4221Publication Date (Print):September 1, 1966Publication History Published online1 May 2002Published inissue 1 September...
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTChemical Transformations of IbogaineG. Büchi and R. E. ManningCite this: J. Am. Chem. Soc. 1966, 88, 11, 2532–2535Publication Date (Print):June 1, 1966Publication History Published online1 May 2002Published inissue 1 June 1966https://pubs.acs.org/doi/10.1021/ja00963a031https://doi.org/10.1021/ja00963a031research-articleACS PublicationsRequest reuse...
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTThe Alkaloids of Tabernanthe iboga. Part IV.1 The Structures of Ibogamine, Ibogaine, Tabernanthine and VoacangineM. F. Bartlett, D. F. Dickel, and W. I. TaylorCite this: J. Am. Chem. Soc. 1958, 80, 1, 126–136Publication Date (Print):January 1, 1958Publication History Published online1 May 2002Published inissue 1 January...
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTIboga Alkaloids. II.1 the Structures of Ibogaine, Ibogamine and TabernanthineW. I. TaylorCite this: J. Am. Chem. Soc. 1957, 79, 12, 3298–3299Publication Date (Print):June 1, 1957Publication History Published online1 May 2002Published inissue 1 June 1957https://pubs.acs.org/doi/10.1021/ja01569a093https://doi.org/10.1021/ja01569a093research-articleACS...
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTCactus Alkaloids. II. Condensation of Mescaline with Formaldehyde by the Eschweiler—Clarke ReactionJosé A. CastrillónCite this: J. Am. Chem. Soc. 1952, 74, 2, 558–559Publication Date (Print):January 1, 1952Publication History Published online1 May 2002Published inissue 1 January...
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTA New Synthesis of MescalineMakepeace U. TsaoCite this: J. Am. Chem. Soc. 1951, 73, 11, 5495–5496Publication Date (Print):November 1, 1951Publication History Published online1 May 2002Published inissue 1 November 1951https://pubs.acs.org/doi/10.1021/ja01155a562https://doi.org/10.1021/ja01155a562research-articleACS PublicationsRequest reuse...
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAn Improved Synthesis of MescalineFred Benington and Richard D. MorinCite this: J. Am. Chem. Soc. 1951, 73, 3, 1353Publication Date (Print):March 1, 1951Publication History Published online1 May 2002Published inissue 1 March 1951https://pubs.acs.org/doi/10.1021/ja01147a505https://doi.org/10.1021/ja01147a505research-articleACS PublicationsRequest reuse...
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTUltraviolet Absorption Spectra of Mescaline Sulfate and β-Phenylethylamine SulfateKurt Salomon and Albert F. BinaCite this: J. Am. Chem. Soc. 1946, 68, 11, 2403Publication Date (Print):November 1, 1946Publication History Published online1 May 2002Published inissue 1 November...