q2K BHP
Black History Portal
THE BHP WIRE —
HIDDEN TRUTHS
GREENWOOD / BLACK WALL STREET WILMINGTON 1898 LITTLE ROCK NINE TUSKEGEE STUDY ROSEWOOD 1923 THE TUSKEGEE AIRMEN SENECA VILLAGE BLACK TOWNS GREENWOOD / BLACK WALL STREET WILMINGTON 1898 LITTLE ROCK NINE TUSKEGEE STUDY ROSEWOOD 1923 THE TUSKEGEE AIRMEN SENECA VILLAGE BLACK TOWNS
What's New!
THE JOURNEY THROUGH TIME
BHP HOME BEFORE AMERICA 1800–1936 1937–1957 1958–1980 1981–2000 2001–PRESENT

Explore Black History

Explore the people, places, events, achievements, struggles and stories that shaped our journey.

✊🏾

Civil Rights

Movements, leaders, victories and the continuing fight for equality.

⚙️

Black Inventors

Innovation, patents, science, technology and world-changing contributions.

🏆

Sports

Pioneers, champions, Negro Leagues, records, activism and excellence.

♟️

People

Meet the people whose lives, choices and achievements shaped the journey.

📍

Places

Black towns, communities, institutions and places where history happened.

📜

Events

Moments that changed communities, movements, institutions and the nation.

Enter a person, place, event, or topic.
MY'STORY

The MOVE Fire

This is a personal recollection on the Move fire on May 13, 1985 Philadelphia police fired thousands of rounds at the MOVE house, city officials approved dropping an explosive device on the roof, the resulting fire was allowed to burn, 11 people—including five children—died, and 61 homes were destroyed. Philadelphia City Council later called it a “brutal attack carried out by the City of Philadelphia on its own citizens” and acknowledged that no individual faced criminal consequences for the bombing. One timeline correction worth preserving for the BHP record: the major previous MOVE-police confrontation was August 8, 1978, about seven years before the bombing, not a year or two earlier. Officer James Ramp was killed, other police and firefighters were wounded, nine MOVE members were later convicted, and television cameras recorded police beating Delbert Africa during his arrest. The 1985 MOVE Commission later specifically criticized city planners for failing to adequately use lessons from that 1978 confrontation. And that actually strengthens the point you’re making: 1985 did not happen without precedent or institutional memory. There had already been a deadly confrontation with MOVE, years of conflict, negotiations and police involvement before Osage Avenue.

MORE →
BLACK FACTS
The Truths They Never Taught You...

Wilmington 1898 — An American Coup

Wilmington, North Carolina once had a thriving Black middle class and an elected interracial government. In 1898 white supremacists used violence to overthrow that government, kill Black residents and drive many others from the city.

MORE →
BHP gathered finds from its connected research sources. Showing the 4 strongest Black History matches.
← BACK TO RESULTS
Wikipedia

2-Iodo-LSD

2-Iodo-LSD
Clinical data
Other namesIodo-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 classSerotonin receptor modulator; Non-hallucinogenic serotonin 5-HT2A receptor modulator
ATC code
  • None
Identifiers
  • (6aR,9R)-N,N-diethyl-5-iodo-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H24IN3O
Molar mass449.336 g·mol−1
3D model (JSmol)
  • CCN(CC)C(=O)[C@H]1CN([C@@H]2CC3=C(NC4=CC=CC(=C34)C2=C1)I)C
  • InChI=1S/C20H24IN3O/c1-4-24(5-2)20(25)12-9-14-13-7-6-8-16-18(13)15(19(21)22-16)10-17(14)23(3)11-12/h6-9,12,17,22H,4-5,10-11H2,1-3H3/t12-,17-/m1/s1
  • Key:OBCUQRYIGTWROI-SJKOYZFVSA-N

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]

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]

Pharmacodynamics

[edit]

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]

[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]

2-Iodo-LSD was described in the scientific literature by Albert Hofmann and colleagues by 1956.[14][15][9][8]

See also

[edit]

References

[edit]
  1. ^ a b c d Nichols DE (2018). "Chemistry and Structure-Activity Relationships of Psychedelics". Current Topics in Behavioral Neurosciences. Vol. 36. pp. 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. PMID 28401524. If a halogen is introduced at the 2-position of LSD, for example in 2-bromo-LSD (BOL-148) or 2-iodo-LSD, the resulting molecules lack hallucinogenic activity and are antagonists at the 5-HT2A receptor. No work with BOL-148 has been reported since the early 1970s, but it was shown that it could block the effects of LSD in humans.(Ginzel and Mayer-Gross 1956) The radiolabeled 2-iodo congener, [125I] 2-iodo-LSD, has been employed as a radioligand for 5-HT2 family receptors (Hartig et al. 1983; Nakada et al. 1984; McKenna et al. 1989; Watts et al. 1994). More recently, BOL has shown efficacy in aborting and/or preventing cluster headaches (Karst et al. 2010).
  2. ^ a b c d Nichols DE (2012). "Structure–activity relationships of serotonin 5-HT 2A agonists" (PDF). Wiley Interdisciplinary Reviews: Membrane Transport and Signaling. 1 (5): 559–579. doi:10.1002/wmts.42. ISSN 2190-460X. Halogenation at the 2-position of LSD as in 2-bromo-LSD (BOL-148) or 2-iodo-LSD leads to molecules that are 5-HT2A antagonists. Although virtually no work has been done with BOL-148 since the early 1970s, it was demonstrated early on that it could block the effects of LSD in humans.26 [125I]2-Iodo-LSD has found application as a radioactive label for 5-HT2 family receptors.27–30
  3. ^ a b c Halberstadt AL, Geyer MA (2013). "[Chapter 61:] Neuropharmacology of Lysergic Acid Diethylamide (LSD) and Other Hallucinogens". In Miller PM, Blume AW, Kavanagh DJ, Kampman KM, Bates ME, Larimer ME, Petry NM, De Witte P, Ball SA (eds.). Biological Research on Addiction: Comprehensive Addictive Behaviors and Disorders. Vol. 2. Elsevier. pp. 625–635. doi:10.1016/b978-0-12-398335-0.00061-3. ISBN 978-0-12-398335-0. Archived from the original on 28 March 2025. There is a complete loss of activity if LSD is brominated or iodinated in the 2-position, and these substances (2-bromo-LSD and 2-iodo-LSD, respectively) act as 5-HT2A antagonists. Consistent with its antagonist activity, pretreatment with 2-bromo-LSD completely blocks the effects of subsequent LSD administration.
  4. ^ a b Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. 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."
  5. ^ Glennon RA (July 2003). "Higher-end serotonin receptors: 5-HT(5), 5-HT(6), and 5-HT(7)". Journal of Medicinal Chemistry. 46 (14): 2795–2812. doi:10.1021/jm030030n. PMID 12825922.
  6. ^ Middlemiss DN, Hibert M, Fozard JR (1986). "Chapter 5. Drugs Acting at Central 5-Hydroxytryptamine Receptors". Annual Reports in Medicinal Chemistry. Vol. 21. Elsevier. pp. 41–50. doi:10.1016/s0065-7743(08)61115-x. ISBN 978-0-12-040521-3. Retrieved 30 June 2025.
  7. ^ Glennon RA, Dukat M (December 1991). "Serotonin receptors and their ligands: a lack of selective agents". Pharmacology, Biochemistry, and Behavior. 40 (4): 1009–1017. doi:10.1016/0091-3057(91)90121-h. PMID 1816555.
  8. ^ a b Cerletti A, Doepfner W (January 1958). "Comparative study on the serotonin antagonism of amide derivatives of lysergic acid and of ergot alkaloids". The Journal of Pharmacology and Experimental Therapeutics. 122 (1): 124–136. doi:10.1016/S0022-3565(25)11933-2. PMID 13502837.
  9. ^ a b Rothlin E (March 1957). "Lysergic acid diethylamide and related substances". Annals of the New York Academy of Sciences. 66 (3): 668–676. Bibcode:1957NYASA..66..668R. doi:10.1111/j.1749-6632.1957.tb40756.x. PMID 13425249.
  10. ^ Hintzen A, Passie T (10 June 2010). The Pharmacology of LSD. OUP/Beckley Foundation Press. p. 19. ISBN 978-0-19-958982-1. Retrieved 30 June 2025. 2-Bromo-lysergic acid diethylamide (BOL-148) The most investigated lysergic acid derivative after LSD is bromo-LSD (BOL-148) (Table 2.3). Whilst the strength of serotonin antagonism with LSD is comparable, it possesses almost no psychic effects (even in doses up to 20 μg/kg). The only psychic effect described was a feeling of tiredness and some psychophysical irritation at high doses (Cerletti & Konzett, 1956). [...] Iodine-LSD is iodinated in position 2 and is only half as effective in relation to psychic effects, as well as to serotonin antagonism, as LSD itself (Cerletti & Konzett, 1956). [...]
  11. ^ Engel G, Müller-Schweinitzer E, Palacios JM (April 1984). "2-[125Iodo]LSD, a new ligand for the characterisation and localisation of 5-HT2 receptors". Naunyn-Schmiedeberg's Archives of Pharmacology. 325 (4): 328–336. doi:10.1007/BF00504377. PMID 6728042.
  12. ^ Cumming P, Scheidegger M, Dornbierer D, Palner M, Quednow BB, Martin-Soelch C (April 2021). "Molecular and Functional Imaging Studies of Psychedelic Drug Action in Animals and Humans". Molecules. 26 (9). Basel, Switzerland: 2451. doi:10.3390/molecules26092451. PMC 8122807. PMID 33922330. N-methyl-2-[125I]-iodo-lysergic acid diethylamide ([125I]-MIL, 24) was developed as a presumably non-hallucinogenic ligand for the molecular imaging of serotonin receptors, whereby N-methylation of [125I]-LSD (25) was intended to impart greater selectivity and sensitivity for 5HT2 receptors [23]. [...] D-(+)-N-ethyl-2-[125I]iodo-lysergic acid diethylamide ([125I]-EIL, 23) was developed as a ligand for molecular imaging of serotonin receptors. [...]
  13. ^ Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4.
  14. ^ Troxler F, Hofmann A (1957). "Substitutionen am Ringsystem der Lysergsäure. III. Halogenierung. 45. Mitteilung über Mutterkornalkaloide". Helvetica Chimica Acta. 40 (7): 2160–2170. Bibcode:1957HChAc..40.2160T. doi:10.1002/hlca.19570400716. ISSN 0018-019X. Retrieved 30 June 2025.
  15. ^ Cerletti A, Konzett H (1956). "Spezifische Hemmung von 5-Oxytryptamin-Effekten durch Lysergsäurediäthylamid und ähnliche Körper" [Specific inhibition of serotonin effects by lysergic acid diethylamide and similar compounds]. Naunyn-Schmiedebergs Archiv für Experimentelle Pathologie und Pharmakologie (in German). 228 (1–2): 146–148. doi:10.1007/BF00259761. PMID 13334586. Substitutionsprodukte des LSD 1. Acetyl-LSD, durch Einfiihrung eines Acetylrestes in 1-Stellung gewonnen, ist etwa 2mal starker 50T-hemmend wirksam. Brom- und Jod-LSD, durch Einffihrung von Brom und Jod in 2-Stellung bereitet, sind 1,5mal starker bzw. 2real schw~cher 50T-hemmend wirksam. Oxymethyl-LSD, durch Einffihrung einer 0xymethylgruppe in 1-Stellung gewonnen, ist 1,5mal schw~icher wirksam.
[edit]

Source: Wikipedia. Article content is retrieved live through the MediaWiki API.

Wikipedia

2-Iodo-LSD

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). It is the 2-iodo derivative of LSD.

MORE →
Wikipedia

Lysergamides

Lysergamides, also known as ergoamides or as lysergic acid amides, are amides of lysergic acid (LA). They are ergolines, with some lysergamides being found naturally in ergot as well as other fungi. Lysergamides are notable in containing embedded phenethylamine and tryptamine moieties within their ergoline ring system. The simplest lysergamides are ergine (lysergic acid amide; LSA) and isoergine (iso-lysergic acid amide; iso-LSA). In terms of pharmacology, the lysergamides include numerous serotonin and dopamine receptor agonists, most notably the psychedelic drug lysergic acid diethylamide (LSD) but also a number of pharmaceutical drugs like ergometrine, methylergometrine, methysergide, and cabergoline. Various analogues of LSD, such as the psychedelics ALD-52 (1A-LSD), ETH-LAD, LSZ, and 1P-LSD and the non-hallucinogenic 2-bromo-LSD (BOL-148), have also been developed. Ergopeptines like ergotamine, dihydroergotamine, and bromocriptine are also lysergamides, but with addition of a small peptide moiety at the amide. Close analogues of lysergamides that are not technically lysergamides themselves include lisuride, terguride, bromerguride, JRT (isotryptamine-LSD), and LSD-Quinoline, among others. Lysergamides were first discovered and described in the 1930s. LSD was first synthesized in 1938 and its psychedelic effects were discovered in 1943. Simplified or partial ergolines and lysergamides, such as NDTDI (8,10-seco-LSD), UCD0120, and N-DEAOP-NMT, are also known.

MORE →
Wikipedia

BOL-148

BOL-148, also known as 2-bromo-LSD or as bromolysergide, is a non-hallucinogenic serotonin receptor modulator of the lysergamide family related to the psychedelic drug lysergic acid diethylamide (LSD). It is specifically the 2-bromo derivative of LSD. The drug is a non- or minimally-hallucinogenic serotonin 5-HT2A receptor partial agonist, as well as acting at other targets such as other serotonin receptors and dopamine receptors. The lack of psychedelic effects with BOL-148 is thought to be due to lower-efficacy partial agonism at the serotonin 5-HT2A receptor compared to LSD that is insufficient to produce hallucinogenic effects. The drug has been found to produce psychoplastogenic and antidepressant-like effects in animals. BOL-148 was initially developed by Albert Hofmann in the 1950s, as part of the original research from which LSD was also derived. It is now being reinvestigated and is under development for the potential treatment of cluster headaches and other conditions. This is under new developmental code names including BETR-001, TD-0148A, and NYPRG-101.

MORE →
Wikipedia

1P-BOL-148

1P-BOL-148, also known as 1-propionyl-2-bromo-LSD or as SYN-L-017, is an analogue of LSD which acts as a prodrug for 2-bromo-LSD (BOL-148). It does not have hallucinogenic effects, but is claimed to be potentially useful for the treatment of cluster headaches, and as an antidepressant.

MORE →
TOPIC OF THE DAY

Greenwood / Black Wall Street

Before the 1921 destruction of Tulsa’s Greenwood District, Black residents had created a remarkable center of business and community life. The district included stores, professional offices, entertainment venues and homes owned by Black citizens. Understanding Greenwood means learning what was built—not only what was burned.

MORE →
TRIVIA QUESTION OF THE DAY

Which Black woman became the first elected to the United States Congress?

Shirley Chisholm, elected in 1968.