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Plakohypaphorines are
halogenated
indolic
non-proteinogenic amino acids named for their similarity to hypaphorine (N,N,N -trimethyltryptophan). First reported in the
Caribbean
sponge Plakortis simplex in 2003, plakohypaphorines A-C were the first iodine-containing indoles to be discovered in nature. Plakohypaphorines D-F , also found in P. simplex , were reported in 2004 by a group including the researchers who discovered the original plakohypaphorines.
Plakohypaphorine
Chemical name
Chemical formula
SMILES
Image
Plakohypaphorine
7-Iodo-N,N,N -trimethyltryptophan
C14 H17 IN2 O2
OC(=O)C(N(C)(C)C)Cc2cnc1c2cccc1I
Plakohypaphorine B
6,7-Diiodo-N,N,N -trimethyltryptophan
C14 H16 I2 N2 O2
OC(=O)C(N(C)(C)C)Cc2cnc1c2ccc(I)c1I
Plakohypaphorine C
5,7-Diiodo-N,N,N -trimethyltryptophan
C14 H16 I2 N2 O2
CN(C)(C)C(C(=O)O)Cc2cnc1c2cc(I)cc1I
Plakohypaphorine D
5,6-Diiodo-N,N,N -trimethyltryptophan
C14 H16 I2 N2 O2
Ic2cc1c(cc2I)ncc1CC(C(O)=O)N(C)(C)C
Plakohypaphorine E
5,6,7-Triiodo-N,N,N -trimethyltryptophan
C14 H15 I3 N2 O2
CN(C)(C)C(C(=O)O)Cc1cnc(c(I)c2I)c1cc2I
Plakohypaphorine F
6-Chloro-5-iodo-N,N,N -trimethyltryptophan
C14 H16 ClIN2 O2
Clc2c1ncc(CC(C(O)=O)N(C)(C)C)c1cc(I)c2
References
Taglialatela-Scafati Orazio et al., 2003. Plakohypaphorines A-C, Iodine-Containing Alkaloids from the Caribbean Sponge Plakortis simplex. European Journal of Organic Chemistry. 2003(2), pp. 284–287.
Borrelli, Francesca, et al., 2004. Iodinated Indole Alkaloids From Plakortis simplex, New Plakohypaphorines and an Evaluation of Their Antihistamine Activity . European Journal of Organic Chemistry. 2004(15), pp. 3227–3232.
1-Methylpsilocin
2,alpha-DMT
2-Me-DET
2-Methyl-5-HT
2,N,N-TMT
4,5-DHP-DMT
4,5-MDO-DMT
4,5-MDO-DiPT
4-AcO-DALT
4-AcO-DET
4-AcO-DMT
4-AcO-DiPT
4-AcO-EPT
4-AcO-NMT
4-AcO-MALT
4-AcO-MET
4-AcO-DPT
4-AcO-MiPT
4-F-5-MeO-DMT
4-HO-5-MeO-DMT
4-HO-DALT
4-HO-DBT
4-HO-DET
4-HO-DiPT
4-HO-DPT
4-HO-DSBT
4-HO-EPT
4-HO-MALT
4-HO-MET
4-HO-McPT
4-HO-McPeT
4-HO-MiPT
4-HO-MPMI
4-HO-MPT
4-HO-MsBT
4-HO-NMT
4-HO-PiPT
4-HO-pyr-T
4-HO-αMT
4-Me-αET
4-Me-αMT
4-MeO-DiPT
4-MeO-DMT
4-MeO-MiPT
4-PrO-DMT
5,6-MeO-MiPT
5,6-MDO-DiPT
5,6-MDO-DMT
5,6-MDO-MiPT
5,7-Dihydroxytryptamine
5-BT
5-Bromo-DMT
5-CT
5-Chloro-αMT
5-Chloro-DMT
5-Ethoxy-αMT
5-Ethoxy-DMT
5-Ethyl-DMT
5-Fluoro-AET
5-Fluoro-αMT
5-Fluoro-DET
5-Fluoro-DMT
5-Fluoro-EPT
5-Fluoro-MET
5-HO-αMT
5-HO-DiPT
5-HTP
5-iPrO-AMT
5-MeS-DMT
5-Methoxytryptamine
5-MeO-7,N,N-TMT
5-Methyl-αET
5-MeO-2-TMT
5-MeO-αET
5-MeO-αMT
5-MeO-DALT
5-MeO-DBT
5-MeO-DET
5-MeO-DiPT
5-MeO-DMT
5-MeO-DPT
5-MeO-EiPT
5-MeO-EPT
5-MeO-MALT
5-MeO-MET
5-MeO-MiPT
5-MeO-MPMI
5-MeO-NMT
5-MeO-pyr-T
5-MeO-NBpBrT
5-Methyl-DMT
5-(Nonyloxy)tryptamine
6-Fluoro-αMT
6-Fluoro-DMT
6-Hydroxymelatonin
6-MeO-THH
7-Chloro-AMT
7-Methyl-α-ethyltryptamine
7-Methyl-DMT
Acetryptine
Aeruginascin
αET
Alpha,N-DMT
α,N,N-Trimethyltryptamine
Alpha,N,O-TMS
AL-37350A
αMT
Baeocystin
BNC-210
Bufotenidine
Bufotenin (5-HO-DMT)
BW-723C86
Convolutindole A
CP-132,484
DALT
DBT
Desformylflustrabromine
DET
DiPT
DPT
E-6801
E-6837
Ethocybin
EiPT
EMDT
EPT
FGIN-127
FGIN-143
Harmaline
HIOC
Ibogaine
Idalopirdine
Indorenate
Iprocin
Lespedamine
Luzindole
MET
Methylbutyltryptamine
MiPT
MPT
Miprocin
Melatonin
MPMI
MS-245
NAS
N-Ethyltryptamine
N-Feruloylserotonin
NMT
DMT
Norbaeocystin
Normelatonin
N-t-Butyltryptamine
O-4310
Oxypertine
Plakohypaphorine
PiPT
Psilocin (4-HO-DMT)
Psilocybin (4-PO-DMT)
Pyr-T
Rizatriptan
RU-28306
Serotonin
ST-1936
Sumatriptan
Tryptamine
Tryptophan
Yohimbine
Yuremamine
Zolmitriptan