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Lysergic acid 2-butyl amide
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| Systematic (IUPAC) name |
| (8β)- 6-methyl- N- [(1R)- 1-methylpropyl]- 9,10- didehydroergoline- 8-carboxamide |
| Clinical data |
| Pregnancy cat. |
? |
| Legal status |
? |
| Identifiers |
| CAS number |
137765-82-3 (R,R) isomer, freebase
137765-83-4 (R,R) isomer, maleate salt |
| ATC code |
? |
| PubChem |
CID 15119692 |
| Synonyms |
(6aR,9R)- N- (R)- 2-butyl- 7-methyl- 4,6,6a,7,8,9- hexahydroindolo- [4,3-fg] quinoline- 9-carboxamide |
| Chemical data |
| Formula |
C20H25N3O |
| Mol. mass |
323.431 g/mol |
- CN2CC(C(=O)NC(C)CC)C=C(C2C3)c1cccc4ncc3c14
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 Y (what is this?) (verify)
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Lysergic acid 2-butyl amide (2-Butyllysergamide, LSB) is an analogue of LSD originally developed by Richard Pioch at Eli Lilly in the 1950s,[1] but mostly publicised through research conducted by the team led by David E. Nichols at Purdue University. It is a structural isomer of LSD, with the two ethyl groups on the amide nitrogen having been replaced by a single butyl group, joined at the 2-position.[2] It is one of the few lysergamide derivatives to exceed the potency of LSD in animal drug discrimination assays, with the (R) isomer having an ED50 of 33nmol/kg for producing drug-appropriate responding, vs 48nmol/kg for LSD itself. The corresponding (R)-2-pentyl analogue has higher binding affinity for the 5-HT1A and 5-HT2A receptors, but is less potent in producing drug-appropriate responding, suggesting that the butyl compound has a higher efficacy at the receptor target.[3] The drug discrimination assay for LSD in rats involves both 5-HT1A and 5-HT2A mediated components, and while lysergic acid 2-butyl amide is more potent than LSD as a 5-HT1A agonist, it is slightly less potent as a 5-HT2A agonist, and so would probably be slightly less potent than LSD as a hallucinogen in humans. The main use for this drug has been in studies of the binding site at the 5-HT2A receptor through which LSD exerts most of its pharmacological effects,[4] with the stereoselective activity of these unsymmetric monoalkyl lysergamides foreshadowing the subsequent development of compounds such as Lysergic acid 2,4-dimethylazetidide.
See also [edit]
References [edit]
- ^ US patent 2997470, Richard P. Pioch, "LYSERGIC ACID AMIDES", published 1956-03-05, issued 1961-08-22
- ^ Oberlender R, Pfaff RC, Johnson MP, Huang XM, Nichols DE. Stereoselective LSD-like activity in d-lysergic acid amides of (R)- and (S)-2-aminobutane. Journal of Medicinal Chemistry. 1992 Jan 24;35(2):203-11. PMID 1732537
- ^ Monte AP, Marona-Lewicka D, Kanthasamy A, Sanders-Bush E, Nichols DE. Stereoselective LSD-like activity in a series of d-lysergic acid amides of (R)- and (S)-2-aminoalkanes. Journal of Medicinal Chemistry. 1995 Mar 17;38(6):958-66. doi:10.1021/jm00006a015 PMID 7699712
- ^ David E. Nichols. LSD and Its Lysergamide Cousins. The Heffter Review of Psychedelic Research. 2001;2:80-87.
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Psychedelics
5-HT2AR agonists |
- Lysergamides: AL-LAD
- ALD-52
- BU-LAD
- CYP-LAD
- DAM-57
- Diallyllysergamide
- Ergometrine
- ETH-LAD
- LAE-32
- LSA
- LSD
- LSH
- LPD-824
- LSM-775
- Lysergic acid 2-butyl amide
- Lysergic acid 2,4-dimethylazetidide
- Lysergic acid 3-pentyl amide
- Methylergometrine
- Methylisopropyllysergamide
- Methysergide
- MLD-41
- PARGY-LAD
- PRO-LAD
Phenethylamines: Aleph
- 2C-B
- 2C-B-Dragonfly
- 2C-B-FLY
- 2C-C-FLY
- 2C-D-FLY
- 2C-E-FLY
- 2C-I-FLY
- 2CBFly-NBOMe
- 2C-T-7-FLY
- 2C-C
- 2C-C-NBOMe
- 2C-CN-NBOMe
- 2C-D
- 2CD-5EtO
- 2C-D-NBOMe
- 2C-E
- 2C-EF
- 2C-E-NBOMe
- 2C-F
- 2C-F-NBOMe
- 2C-G
- 2C-G-NBOMe
- 2C-H-NBOMe
- 2C-I
- 2C-N
- 2C-N-NBOMe
- 2C-O
- 2C-O-4
- 2C-P
- 2C-T
- 2C-T-2
- 2C-T-4
- 2C-T-4-NBOMe
- 2C-T-7
- 2C-T-7-NBOH
- 2C-T-8
- 2C-T-9
- 2C-T-13
- 2C-T-15
- 2C-T-17
- 2C-T-21
- 2C-TFM
- 2C-TFM-NBOMe
- 2C-YN
- 2CBCB-NBOMe
- 25B-NBOMe
- 25I-NBMD
- 25I-NBOH
- 25I-NBOMe
- 3C-AL
- 3C-E
- 3C-P
- 5-APB
- 5-APDB
- 6-APB
- 6-APDB
- Br-DFLY
- DESOXY
- DMMDA
- DMMDA-2
- DOB
- DOB-FLY
- DOM-FLY
- DOC
- DOEF
- DOET
- DOF
- DOI
- DOM
- DON
- DOPR
- DOTFM
- Escaline
- Ganesha
- HOT-2
- HOT-7
- HOT-17
- IAP
- Isoproscaline
- Jimscaline
- Lophophine
- MDA
- MDEA
- MDMA
- MMA
- MMDA
- MMDA-2
- MMDA-3a
- MMDMA
- Macromerine
- Mescaline
- Methallylescaline
- NBOMe-mescaline
- Proscaline
- TCB-2
- TFMFly
- TMA
Piperazines: pFPP
- TMFPP
Tryptamines: 1-Methyl-5-methoxy-diisopropyltryptamine
- 2,N,N-TMT
- 4,N,N-TMT
- 4-HO-5-MeO-DMT
- 4-Acetoxy-DET
- 4-Acetoxy-DIPT
- 4-Acetoxy-DMT
- 4-Acetoxy-DPT
- 4-Acetoxy-MiPT
- 4-HO-DPT
- 4-HO-MET
- 4-Propionyloxy-DMT
- 4-HO-MPMI
- 5-Me-MIPT
- 5-N,N-TMT
- 5-AcO-DMT
- 5-MeO-2,N,N-TMT
- 5-MeO-4,N,N-TMT
- 5-MeO-α,N,N-TMT
- 5-MeO-α-ET
- 5-MeO-α-MT
- 5-MeO-DALT
- 5-MeO-DET
- 5-MeO-DIPT
- 5-MeO-DMT
- 5-MeO-DPT
- 5-MeO-EiPT
- 5-MeO-MET
- 5-MeO-MIPT
- 5-MeO-MPMI
- 7,N,N-TMT
- α,N,N-TMT
- α-ET
- α-MT
- AL-37350A
- Baeocystin
- Bufotenin
- DALT
- DBT
- DCPT
- DET
- DIPT
- DMT
- DPT
- EiPT
- Ethocin
- Ethocybin
- Iprocin
- MET
- Miprocin
- MIPT
- Norbaeocystin
- PiPT
- Psilocin
- Psilocybin
Others: AL-38022A
- Elemicin
- Ibogaine
- Myristicin
- Noribogaine
- Voacangine
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Dissociatives
NMDAR antagonists |
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Deliriants
mAChR antagonists |
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| Miscellaneous |
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- Agonists: Azapirones: Alnespirone
- Binospirone
- Buspirone
- Enilospirone
- Eptapirone
- Gepirone
- Ipsapirone
- Perospirone
- Revospirone
- Tandospirone
- Tiospirone
- Umespirone
- Zalospirone; Antidepressants: Etoperidone
- Nefazodone
- Trazodone
- Vortioxetine; Antipsychotics: Aripiprazole
- Asenapine
- Clozapine
- Quetiapine
- Ziprasidone; Ergolines: Dihydroergotamine
- Bromocriptine
- Ergotamine
- Lisuride
- Methysergide
- LSD; Tryptamines: 5-CT
- 5-MeO-DMT
- 5-MT
- Bufotenin
- DMT
- Indorenate
- Psilocin
- Psilocybin; Others: 8-OH-DPAT
- Adatanserin
- Bay R 1531
- Befiradol
- BMY-14802
- Cannabidiol
- Dimemebfe
- Ebalzotan
- Eltoprazine
- F-11,461
- F-12,826
- F-13,714
- F-14,679
- F-15,063
- F-15,599
- Flesinoxan
- Flibanserin
- Lesopitron
- LY-293,284
- LY-301,317
- MKC-242
- Naluzotan
- NBUMP
- Osemozotan
- Oxaflozane
- Pardoprunox
- Piclozotan
- Rauwolscine
- Repinotan
- Roxindole
- RU-24,969
- S 14,506
- S-14,671
- S-15,535
- Sarizotan
- SSR-181,507
- Sunepitron
- U-92,016-A
- Urapidil
- Vilazodone
- Xaliproden
- Yohimbine
Antagonists: Antipsychotics: Iloperidone
- Risperidone
- Sertindole; Beta blockers: Alprenolol
- Cyanopindolol
- Iodocyanopindolol
- Oxprenolol
- Pindobind
- Pindolol
- Propranolol
- Tertatolol; Others: AV965
- BMY-7,378
- CSP-2503
- Dotarizine
- Flopropione
- GR-46611
- Isamoltane
- Lecozotan
- Mefway
- Metitepine/Methiothepin
- MPPF
- NAN-190
- Robalzotan
- S-15535
- SB-649,915
- SDZ 216-525
- Spiperone
- Spiramide
- Spiroxatrine
- UH-301
- WAY-100,135
- WAY-100,635
- Xylamidine
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- Agonists: Lysergamides: Dihydroergotamine
- Methysergide; Triptans: Almotriptan
- Avitriptan
- Eletriptan
- Frovatriptan
- Naratriptan
- Rizatriptan
- Sumatriptan
- Zolmitriptan; Tryptamines: 5-CT
- 5-Ethyl-DMT
- 5-MT
- 5-(Nonyloxy)tryptamine; Others: CP-135,807
- Bromocriptine
- CP-286,601
- GR-46611
- L-694,247
- L-772,405
- PNU-109,291
- PNU-142633
Antagonists: Lysergamides: Metergoline; Others: Alniditan
- BRL-15,572
- Elzasonan
- GR-127,935
- Ketanserin
- LY-310,762
- LY-367,642
- LY-456,219
- LY-456,220
- Metitepine/Methiothepin
- Ritanserin
- Yohimbine
- Ziprasidone
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- Agonists: Phenethylamines: 2C-B
- 2C-E
- 2C-I
- 2C-T-2
- 2C-T-7
- 2C-T-21
- DOB
- DOC
- DOI
- DOM
- MDA
- MDMA
- Mescaline; Piperazines: Aripiprazole
- mCPP
- TFMPP; Tryptamines: 5-CT
- 5-MeO-α-ET
- 5-MeO-α-MT
- 5-MeO-DET
- 5-MeO-DiPT
- 5-MeO-DMT
- 5-MeO-DPT
- 5-MT
- α-ET
- α-Methyl-5-HT
- α-MT
- Bufotenin
- DET
- DiPT
- DMT
- DPT
- Psilocin
- Psilocybin; Others: A-372,159
- Bromocriptine
- AL-38022A
- CP-809,101
- Dimemebfe
- Lorcaserin
- Medifoxamine
- MK-212
- Org 12,962
- ORG-37,684
- Oxaflozane
- PNU-22394
- Ro60-0175
- Ro60-0213
- Vabicaserin
- WAY-629
- WAY-161,503
- YM-348
Antagonists: Atypical antipsychotics: Clorotepine
- Clozapine
- Iloperidone
- Melperone
- Olanzapine
- Paliperidone
- Pimozide
- Quetiapine
- Risperidone
- Sertindole
- Ziprasidone
- Zotepine; Typical antipsychotics: Chlorpromazine
- Loxapine
- Pipamperone; Antidepressants: Agomelatine
- Amitriptyline
- Amoxapine
- Aptazapine
- Etoperidone
- Fluoxetine
- Mianserin
- Mirtazapine
- Nefazodone
- Nortriptyline
- Tedatioxetine
- Trazodone; Others: Adatanserin
- CEPC
- Cinanserin
- Cyproheptadine
- Deramciclane
- Dotarizine
- Eltoprazine
- Esmirtazapine
- FR-260,010
- Ketanserin
- Ketotifen
- Latrepirdine
- Metitepine/Methiothepin
- Methysergide
- Pizotifen
- Ritanserin
- RS-102,221
- S-14,671
- SB-200,646
- SB-206,553
- SB-221,284
- SB-228,357
- SB-242,084
- SB-243,213
- SDZ SER-082
- Xylamidine
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- Agonists: Lysergamides: Dihydroergotamine
- Ergotamine
- Lisuride
- LSD
- Mesulergine
- Metergoline
- Methysergide; Tryptamines: 2-Methyl-5-HT
- 5-BT
- 5-CT
- 5-MT
- Bufotenin
- E-6801
- E-6837
- EMD-386,088
- EMDT
- LY-586,713
- N-Methyl-5-HT
- Tryptamine; Others: WAY-181,187
- WAY-208,466
Antagonists: Antidepressants: Amitriptyline
- Amoxapine
- Clomipramine
- Doxepin
- Mianserin
- Nortriptyline; Atypical antipsychotics: Aripiprazole
- Asenapine
- Clorotepine
- Clozapine
- Fluperlapine
- Iloperidone
- Olanzapine
- Tiospirone; Typical antipsychotics: Chlorpromazine
- Loxapine; Others: BGC20-760
- BVT-5182
- BVT-74316
- Cerlapirdine
- EGIS-12,233
- GW-742,457
- Ketanserin
- Latrepirdine
- Lu AE58054
- Metitepine/Methiothepin
- MS-245
- PRX-07034
- Ritanserin
- Ro04-6790
- Ro 63-0563
- SB-258,585
- SB-271,046
- SB-357,134
- SB-399,885
- SB-742,457
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- Agonists: Lysergamides: LSD; Tryptamines: 5-CT
- 5-MT
- Bufotenin; Others: 8-OH-DPAT
- AS-19
- Bifeprunox
- E-55888
- LP-12
- LP-44
- RU-24,969
- Sarizotan
Antagonists: Lysergamides: 2-Bromo-LSD
- Bromocriptine
- Dihydroergotamine
- Ergotamine
- Mesulergine
- Metergoline
- Methysergide; Antidepressants: Amitriptyline
- Amoxapine
- Clomipramine
- Imipramine
- Maprotiline
- Mianserin; Atypical antipsychotics: Amisulpride
- Aripiprazole
- Clorotepine
- Clozapine
- Olanzapine
- Risperidone
- Sertindole
- Tiospirone
- Ziprasidone
- Zotepine; Typical antipsychotics: Chlorpromazine
- Loxapine; Others: Butaclamol
- EGIS-12,233
- Ketanserin
- LY-215,840
- Metitepine/Methiothepin
- Pimozide
- Ritanserin
- SB-258,719
- SB-258,741
- SB-269,970
- SB-656,104
- SB-656,104-A
- SB-691,673
- SLV-313
- SLV-314
- Spiperone
- SSR-181,507
- Vortioxetine
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