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NBOMe-LAD

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NBOMe-LAD
Clinical data
Other namesLAD-NBOMe; LSD-NBOMe; NBOMe-LSD; (2-Methoxybenzyl)-LSD; N,N-Diethyl-6-[(2-methoxyphenyl)methyl]-9,10-didehydroergoline-8β-carboxamide
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • (6aR,9R)-N,N-diethyl-7-[(2-methoxyphenyl)methyl]-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
PubChem CID
Chemical and physical data
FormulaC27H31N3O2
Molar mass429.564 g·mol−1
3D model (JSmol)
  • CCN(CC)C(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)CC5=CC=CC=C5OC
  • InChI=1S/C27H31N3O2/c1-4-29(5-2)27(31)20-13-22-21-10-8-11-23-26(21)19(15-28-23)14-24(22)30(17-20)16-18-9-6-7-12-25(18)32-3/h6-13,15,20,24,28H,4-5,14,16-17H2,1-3H3/t20-,24-/m1/s1
  • Key:HPPSQDRSAGTANP-HYBUGGRVSA-N

NBOMe-LAD, also known as LSD-NBOMe, is a serotonin receptor modulator and putative psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD).[1] It is the N-(2-methoxybenzyl) (NBOMe) derivative of LSD.[1]

The drug is known to act as an agonist of the serotonin 5-HT2A receptor and to interact with other receptors, but shows dramatically reduced potency compared to LSD in vitro.[1] At the serotonin 5-HT2A receptor, it had 37-fold lower affinity, 148-fold lower activational potency in terms of calcium release, and around half the maximal efficacy in terms of calcium release relative to LSD.[1] On the other hand, NBOMe-LAD had only about 4-fold lower potency in terms of β-arrestin recruitment along with similar activational efficacy for this pathway relative to LSD.[1]

NBOMe-LAD produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, but with greatly reduced potency and maximal efficacy relative to PRO-LAD and analogues.[1] Its ED50Tooltip median effective dose for inducing the head-twitch response was 13-fold lower than that of PRO-LAD and its maximal effect was about one-third that of PRO-LAD.[1] However, the most efficacious dose of NBOMe-LAD was 3.2 mg/kg whereas that of PRO-LAD was 1 mg/kg.[1]

NBOMe-LAD showed much faster metabolism than LSD in human and rat liver microsomes in vitro.[1]

NBOMe-LAD was first described in the literature by 2022.[1] It was described in a patent by Andrew Kruegel and Gilgamesh Pharmaceuticals.[1] Various other NBOMe-type analogues of LSD and related compounds were also described.[1]

See also

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References

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  1. ^ a b c d e f g h i j k l "Novel ergolines and methods of treating mood disorders". Google Patents. 25 April 2022. Example 10: Preparation of (6aR,9R)-N,N-diethyl-7-(2-methoxybenzyl)-4,6,6a,7,8,9- hexahydroindolo[4,3-fg]quinoline-9-carboxamide (10) [...] Table 3. Results of 5-HT2A and 5-HT2B receptor binding affinity experiments. [...] Table 4. Agonist activity of compounds at select serotonin receptors in Ca2+ flux (5-HT2A, 2B, 2C, and 1A) and cAMP (5-HT1B) functional assays. [...] Table 5. Agonist activity of compounds at the 5-HT2A receptor in an arrestin recruitment assay. [...] Table 6. Agonist activity of compounds at other monoamine receptors in Ca2+ flux functional assays. [...] Table 7. Effects of disclosed compounds in the mouse HTR assay. [...]
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