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2-Iodo-LSD; (8β)-N,N-Diethyl-2-iodo-6-methyl-9,10-didehydroergoline-8-carboxamide
5306
Variant: R1 R2 all
Analogues: 1 2 3

IUPAC: (8β)-N,N-Diethyl-2-iodo-6-methyl-9,10-didehydroergoline-8-carboxamide

Formula: C20H24IN3O Molecular weight: 449.32853 g/mol InChI Key: OBCUQRYIGTWROI-SJKOYZFVSA-N

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

PubChem CID: 151142; ChemSpider: 133214

See also TiHKAL: #26 LSD        
One R1 analogue:
5308
Analogue 1: Adding Methyl at R1

2-Iodo-1-methyl-LSD
MIL
N,N-Diethyl-2-iodo-1-methyllysergamide

IUPAC: (8β)-N,N-Diethyl-2-iodo-1,6-dimethyl-9,10-didehydroergoline-8-carboxamide

Formula: C21H26IN3O Molecular weight: 463.35511 g/mol InChI Key: TWQOQCUIXUGDKO-FZKQIMNGSA-N

InChI=1S/C21H26IN3O/c1-5-25(6-2)21(26)13-10-15-14-8-7-9-17-19(14)16(20(22)24(17)4)11-18(15)23(3)12-13/h7-10,13,18H,5-6,11-12H2,1-4H3/t13-,18-/m1/s1

PubChem CID: 126269; ChemSpider: 112233

See also TiHKAL: #26 LSD        
Two R2 analogues:
5026
Analogue 1: Removing Iodo at R2

LSD
LSD-25
METH-LAD
Acid
N,N-Diethyllysergamide
Lysergide
d-Lysergic acid diethylamide
d-Lysergamide, N,N-diethyl
N,N-Diethyl-d-lysergamide
9,10-Didehydro-N,N-diethyl-6-methylergoline-8β-carboxamide

IUPAC: (8β)-N,N-Diethyl-6-methyl-9,10-didehydroergoline-8-carboxamide

Formula: C20H25N3O Molecular weight: 323.432 g/mol InChI Key: VAYOSLLFUXYJDT-RDTXWAMCSA-N

InChI=1S/C20H25N3O/c1-4-23(5-2)20(24)14-9-16-15-7-6-8-17-19(15)13(11-21-17)10-18(16)22(3)12-14/h6-9,11,14,18,21H,4-5,10,12H2,1-3H3/t14-,18-/m1/s1

PubChem CID: 5761; ChemSpider: 5558; Drugs Forum: LSD; Erowid: LSD; Wikipedia: Lysergic acid diethylamide

See also PiHKAL: #5 ALEPH-4
#6 ALEPH-6
#7 ALEPH-7
#9 ASB
#21 3C-BZ
#25 3C-E
#28 2C-G-3
#30 2C-G-5
#31 2C-G-N
#41 2C-T-4
#43 2C-T-7
#52 DESOXY
#58 DMMDA
#62 DOB
#66 DOET
#67 DOI
#68 DOM
#69 Ψ-DOM
#79 F-2
#80 F-22
#81 FLEA
#97 4-MA
#100 MDA
#101 MDAL
#108 MDIP
#111 MDMEO
#118 MDPR
#125 META-DOT
#132 MMDA
#134 MMDA-3a
#156 4-TM
#160 TMA-4
#161 TMA-5
#170 5-TOET
See also TiHKAL: #1 AL-LAD
#2 DBT
#6 DMT
#9 DPT
#12 ETH-LAD
#16 4-HO-DET
#17 4-HO-DIPT
#18 4-HO-DMT
#19 5-HO-DMT
#28 4,5-MDO-DIPT
#37 5-MeO-DIPT
#48 α-MT
#51 PRO-LAD
#53 T
#57 DALT
See also Pharmacology notes II: app. 2, Abuse week
p. 214, LSD: A recalibration
p. 247, LSD: Window exploitation studies
p. 249, LSD: Window exploitation studies
p. 256, LSD: Window exploitation studies
p. 267, LSD: Window exploitation studies
p. 269, LSD: Calibration
p. 288, LSD: Primer studies
p. 317, LSD: Primer studies

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Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

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McKenna, DJ; Saavedra, JM. Autoradiography of LSD and 2,5-dimethoxyphenylisopropylamine psychotomimetics demonstrates regional, specific cross-displacement in the rat brain. Eur. J. Pharmacol., 13 Oct 1987, 142 (2), 313–315. 263 kB. doi:10.1016/0014-2999(87)90121-X

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5305
Analogue 2: Substituting Bromo for Iodo at R2

BOL-148
2-Bromo-LSD
2-Bromo-N,N-diethyllysergamide

IUPAC: (8β)-2-Bromo-N,N-diethyl-6-methyl-9,10-didehydroergoline-8-carboxamide

Formula: C20H24BrN3O Molecular weight: 402.32806 g/mol InChI Key: VKRAXSZEDRWLAG-SJKOYZFVSA-N

InChI=1S/C20H24BrN3O/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

PubChem CID: 10171; ChemSpider: 9765

See also TiHKAL: #26 LSD        

Abramson, HA. Lysergic acid diethylamide (LSD-25) XXXI. Comparison by questionnaire of psychotomimetic activity of congeners on normal subjects and drug addicts. Br. J. Psychiatry, 1 Jul 1960, 106 (444), 1120–1123. 425 kB. doi:10.1192/bjp.106.444.1120

Ginzel, KH; Mayer-Gross, W. Prevention of psychological effects of d-lysergic acid diethylamide (LSD 25) by its 2-brom derivative (BOL 148). Nature, 28 Jul 1956, 178 (4526), 210. 129 kB. doi:10.1038/178210a0

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