Lysergamides
Appearance
(Redirected from Methylpropyllysergamide)
Amides of lysergic acid are collectively known as lysergamides, and include a number of compounds with potent agonist and/or antagonist activity at various serotonin and dopamine receptors. Lysergamides contain an embedded tryptamine structure, and as a result can produce similar, often psychedelic, effects to those of the true tryptamines. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15]
![](http://upload.wikimedia.org/wikipedia/commons/thumb/3/39/Lysergamides.svg/223px-Lysergamides.svg.png)
Structure | Name | CAS number | R1 | R6 | R2 | R3 | Other |
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LSA / LAA | 478-94-4 | H | CH3 | H | H | - |
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DAM-57 | 4238-84-0 | H | CH3 | CH3 | CH3 | - |
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Ergometrine (Ergonovine) | 60-79-7 | H | CH3 | CH(CH3)CH2OH | H | - |
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Ergotamine | 113-15-5 | H | CH3 | -- | C17H18N2O4 | - |
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Methergine | 113-42-8 | H | CH3 | CH(CH2CH3)CH2OH | H | - |
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Methysergide | 361-37-5 | CH3 | CH3 | CH(CH2CH3)CH2OH | H | - |
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Amesergide | 121588-75-8 | CH(CH3)2 | CH3 | C6H11 | H | - |
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LY-215840 | 137328-52-0 | CH(CH3)2 | CH3 | C5H8OH | H | - |
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Cabergoline | 81409-90-7 | H | H2C=CH-CH2 | CONHCH2CH3 | CH2CH2CH2N(CH3)2 | - |
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LAE-32 | 478-99-9 | H | CH3 | CH2CH3 | H | - |
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LAiP | H | CH3 | CH(CH3)2 | H | - | |
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LAtB | H | CH3 | C(CH3)3 | H | - | |
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LAcB | H | CH3 | (CH2)4 | H | - | |
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Cepentil | H | CH3 | (CH2)5 | H | - | |
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LSB | 137765-82-3 | H | CH3 | CH(CH3)CH2CH3 | H | - |
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LSP | H | CH3 | CH(CH2CH3)CH2CH3 | H | - | |
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DAL | H | CH3 | H2C=CH-CH2 | H2C=CH-CH2 | - | |
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MIPLA | 100768-08-9 | H | CH3 | CH(CH3)2 | CH3 | - |
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EIPLA | H | CH3 | CH(CH3)2 | CH2CH3 | - | |
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ECPLA | H | CH3 | C3H5 | CH2CH3 | - | |
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ETFELA | H | CH3 | CH2CF3 | CH2CH3 | - | |
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LAMPA | 40158-98-3 | H | CH3 | CH2CH2CH3 | CH3 | - |
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EPLA | H | CH2CH3 | CH2CH2CH3 | CH3 | - | |
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LSD / LAD | 50-37-3 | H | CH3 | CH2CH3 | CH2CH3 | - |
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ETH-LAD | 65527-62-0 | H | CH2CH3 | CH2CH3 | CH2CH3 | - |
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PARGY-LAD | H | HC≡C−CH2 | CH2CH3 | CH2CH3 | - | |
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AL-LAD | 65527-61-9 | H | H2C=CH-CH2 | CH2CH3 | CH2CH3 | - |
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PRO-LAD | 65527-63-1 | H | CH2CH2CH3 | CH2CH3 | CH2CH3 | - |
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IP-LAD | H | CH(CH3)2 | CH2CH3 | CH2CH3 | - | |
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CYP-LAD[16] | H | C3H5 | CH2CH3 | CH2CH3 | - | |
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BU-LAD | 96930-87-9 | H | CH2CH2CH2CH3 | CH2CH3 | CH2CH3 | - |
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FLUORETH-LAD[17] | H | CH2CH2F | CH2CH3 | CH2CH3 | - | |
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ALD-52 | 3270-02-8 | COCH3 | CH3 | CH2CH3 | CH2CH3 | - |
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1P-LSD | 2349358-81-0 | COCH2CH3 | CH3 | CH2CH3 | CH2CH3 | - |
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1B-LSD | 2349376-12-9 | COCH2CH2CH3 | CH3 | CH2CH3 | CH2CH3 | - |
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1V-LSD | CO(CH2)3CH3 | CH3 | CH2CH3 | CH2CH3 | - | |
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1DD-LSD | CO(CH2)10CH3 | CH3 | CH2CH3 | CH2CH3 | - | |
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1cP-LSD[18] | COC3H5 | CH3 | CH2CH3 | CH2CH3 | - | |
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1D-LSD | COC4H5(CH3)2 | CH3 | CH2CH3 | CH2CH3 | - | |
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1T-LSD | COC4H3S | CH3 | CH2CH3 | CH2CH3 | - | |
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1S-LSD | CO(CH2)2Si(CH3)3 | CH3 | CH2CH3 | CH2CH3 | - | |
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1P-AL-LAD | COCH2CH3 | H2C=CH-CH2 | CH2CH3 | CH2CH3 | - | |
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1cP-AL-LAD | COC3H5 | H2C=CH-CH2 | CH2CH3 | CH2CH3 | - | |
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1T-AL-LAD[19] | COC4H3S | H2C=CH-CH2 | CH2CH3 | CH2CH3 | - | |
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1P-ETH-LAD | COCH2CH3 | CH2CH3 | CH2CH3 | CH2CH3 | - | |
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1P-MIPLA | COCH2CH3 | CH3 | CH(CH3)2 | CH3 | - | |
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MLD-41 | 4238-85-1 | CH3 | CH3 | CH2CH3 | CH2CH3 | - |
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LSM-775 | 4314-63-0 | H | CH3 | CH2CH2-O-CH2CH2 | - | |
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LPD-824 | 2385-87-7 | H | CH3 | (CH2)4 | - | |
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LSD-Pip | 50485-23-9 | H | CH3 | (CH2)5 | - | |
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LSD-Azapane | H | CH3 | (CH2)6 | - | ||
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LA-SS-Az | 470666-31-0 | H | CH3 | CH2(CHCH3)2CH2 | - | |
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2-Bromo-LSD | 478-84-2 | H | CH3 | CH2CH3 | CH2CH3 | 2-Br |
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12-Methoxy-LSD[20] | 50484-99-6 | H | CH3 | CH2CH3 | CH2CH3 | 12-OMe |
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13-Fluoro-LSD[21] | H | CH3 | CH2CH3 | CH2CH3 | 13-F | |
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14-Hydroxy-LSD[22] | H | CH3 | CH2CH3 | CH2CH3 | 14-OH |
See also
[edit]References
[edit]- ^ Hofmann A (June 1959). "Psychotomimetic drugs; chemical and pharmacological aspects". Acta Physiologica et Pharmacologica Neerlandica. 8: 240–58. PMID 13852489.
- ^ US patent 2997470, Pioch RP, "LYSERGIC ACID AMIDES", published 1956-03-05, issued 1961-08-22
- ^ Hoffman AJ, Nichols DE (September 1985). "Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives". Journal of Medicinal Chemistry. 28 (9): 1252–1255. doi:10.1021/jm00147a022. PMID 4032428.
- ^ Huang X, Marona-Lewicka D, Pfaff RC, Nichols DE (March 1994). "Drug discrimination and receptor binding studies of N-isopropyl lysergamide derivatives". Pharmacology, Biochemistry, and Behavior. 47 (3): 667–673. doi:10.1016/0091-3057(94)90172-4. PMID 8208787. S2CID 16490010.
- ^ Watts VJ, Lawler CP, Fox DR, Neve KA, Nichols DE, Mailman RB (April 1995). "LSD and structural analogs: pharmacological evaluation at D1 dopamine receptors". Psychopharmacology. 118 (4): 401–409. doi:10.1007/BF02245940. PMID 7568626. S2CID 21484356.
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- ^ Nichols DE (2017). "Chemistry and Structure-Activity Relationships of Psychedelics". Current Topics in Behavioral Neurosciences. 36: 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. PMID 28401524.
- ^ Brandt SD, Kavanagh PV, Westphal F, Stratford A, Elliott SP, Hoang K, et al. (September 2016). "Return of the lysergamides. Part I: Analytical and behavioural characterization of 1-propionyl-d-lysergic acid diethylamide (1P-LSD)". Drug Testing and Analysis. 8 (9): 891–902. doi:10.1002/dta.1884. PMC 4829483. PMID 26456305.
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- ^ Brandt SD, Kavanagh PV, Twamley B, Westphal F, Elliott SP, Wallach J, et al. (February 2018). "Return of the lysergamides. Part IV: Analytical and pharmacological characterization of lysergic acid morpholide (LSM-775)". Drug Testing and Analysis. 10 (2): 310–322. doi:10.1002/dta.2222. PMC 6230476. PMID 28585392.
- ^ Brandt SD, Kavanagh PV, Westphal F, Stratford A, Elliott SP, Dowling G, et al. (August 2019). "Return of the lysergamides. Part V: Analytical and behavioural characterization of 1-butanoyl-d-lysergic acid diethylamide (1B-LSD)". Drug Testing and Analysis. 11 (8): 1122–1133. doi:10.1002/dta.2613. PMC 6899222. PMID 31083768.
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