2-Iodo-LSD
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| Other names | Iodo-LSD; Iodine-LSD; IOL; 2-Iodolysergic acid diethylamide; 2-Iodo-N,N-diethyllysergamide; N,N-Diethyl-2-iodo-6-methyl-9,10-didehydroergoline-8β-carboxamide |
| Drug class | Serotonin receptor modulator; Non-hallucinogenic serotonin 5-HT2A receptor modulator |
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| E number | {{#property:P628}} |
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| ECHA InfoCard | {{#property:P2566}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value). |
| Chemical and physical data | |
| Formula | C20H24IN3O |
| Molar mass | 449.336 g·mol−1 |
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2-Iodo-LSD (IOL) is a putatively non-hallucinogenic serotonin receptor modulator of the lysergamide family related to 2-bromo-LSD (BOL-148) and lysergic acid diethylamide (LSD).[1][2][3] It is the 2-iodo derivative of LSD.[1][2][3]
Use and effects
[edit | edit source]According to Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved), it is unknown whether 2-iodo-LSD has ever been tested in humans.[4]
Pharmacology
[edit | edit source]Pharmacodynamics
[edit | edit source]2-Iodo-LSD shows high affinity for the serotonin 5-HT2 receptors and also shows affinity for other serotonin receptors as well as for the dopamine and adrenergic receptors.[5][6] In contrast to LSD, but similarly to 2-bromo-LSD, 2-iodo-LSD is predominantly antagonistic at the serotonin 5-HT2A and 5-HT2C receptors and is described as non-hallucinogenic.[1][2][3][7] The drug has about 57.4% of the antiserotonergic activity of LSD in the isolated rat uterus in vitro, whereas 2-bromo-LSD has about 103% of LSD's potency in this assay.[8][9][10]
Radiolabeling
[edit | edit source][125I]2-Iodo-LSD, a radiolabeled analogue of 2-iodo-LSD, has been used as a radioligand for serotonin 5-HT2 receptors.[4][1][2][11] In addition, radiolabeled derivatives of 2-iodo-LSD, such as 1-methyl-2-[125I]iodo-LSD ([125I]-MIL) and 1-ethyl-2-[125I]iodo-LSD ([125I]-EIL), have been developed for use as presumably non-hallucinogenic agents in imaging of serotonin receptors.[12][13]
History
[edit | edit source]2-Iodo-LSD was described in the scientific literature by Albert Hofmann and colleagues by 1956.[14][15][9][8]
See also
[edit | edit source]- Substituted lysergamide
- 2-Bromo-LSD (BOL-148)
- MBL-61 (1-methyl-2-bromo-LSD)
- 2-Oxo-LSD
References
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- ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value). https://erowid.org/library/books_online/tihkal/tihkal26.shtml "1-Hydroxymethyl-LSD, 1-dimethylaminomethyl-LSD and 2-iodo-LSD. These three additional compounds are shown here because they were described in a synthetic flurry that followed the discovery the activity of LSD. But at the moment I know neither their internal Sandoz codes nor if they had ever been explored in man. This is a kind of frustrating catch-all entry, in that the long index will send you here, and once here you realize that nothing is known. Well, at least the compounds are known, and perhaps there is something in the Sandoz vaults that might be interesting. I do not have access to them. [...] I was at a meeting of a NIDA study section a few years ago, where some one presented some findings with a group of subjects who were complaining of continuing mental problems allegedly due to LSD exposure. A chart was put up showing the outline of the brain showing the locations of the EEG foci that were observed in one of these subjects. Along side it was a PET scan showing the distribution of radioactive LSD in a subject. The purpose was to discuss the similarities and differences of the coordinates of electrical activity and radio-isotope concentration. I innocently asked what positron isotope had been used, as I did not know of any successful positron labelling of LSD. Carbon 11, I was told. Where in the molecule was the label incorporated, I asked. In the 1-position methyl group. It was finally acknowledged that the compound that had actually been used was 2-iodo-1-methyl-LSD, our MIL compound, which is quite a different world. A pharmacologist might say that they are similar in action (looking at serotonin, not psychedelic action), and a chemist might say they are of similar structure (looking at the upper 80% of the molecule. But they are different compounds. This is a most subtle form of deceit. It is, in fact, out and out dishonest, but it looks good up there on the screen at a lecture."
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