And again thanks for this interesting thread nen!
Im attaching the paper quoted by nen in the first post:
Secondary Metabolites from Three Florida Sponges with Antidepressant Activity
J. Nat. Prod., 2008, 71 (2), pp 186โ189
Kochanowska et al
Im also attaching the Hu et al paper about brominated tryptamines and 5-ht2 binding.
Also a bit more info to add (from
Trout's Notes on simple tryptamines), plus molecular structures:
General safety note: Marine organisms often contain toxic/poisonous material. Wear protective clothing, do not bioassay plants without being fully aware of the components found and what you are doing. Also do note that evaluation of gramine analogs suggests 5-bromo compounds may be more toxic than parent compounds Interesting fact: Hydrogenation of 5-Br-DMT and 5,6-dibromo-DMT gave DMT (Djura et al 1980)
5-Bromo-DMT
Soluble in ethanol, DCM, ethyl acetate
Activity: Unknown psychoactivity. Brominated tryptamines show a high affinity for human serotonin receptors (Hu et al. 2002. )
5-Br-DMT caused significant reduction of locomotor activity in the rodent FST model (suggested to indicate a potential sedative action). It did not show any antidepressant activity in either test. (Kochanowska et al. 2008 )
Sources:
Smenospongia aurea - collected in belize, only found in one of the two specimens collected at 0.68% dry weight, postulated it might be produced from symbionts that are not in all places where sponge grow (Djura et al 1980). Nen also posted the Tymiak et al reference.
Eudisoma fragum - sea-squirt from New Caledonia, 0.02% dry weight (Debitus et al 1988 )
Verongula rigida contained 5-Br-DMT (0.00142% dry wt.) (Kochanowska et al. 2008 )
5,6-dibromo-tryptamine
Activity: Unknown psychoactivity. Brominated tryptamines show a high affinity for human serotonin receptors (Hu et al. 2002. )
Shows antibiotic activity against gram negative and gram positive bacteria in vitro but not in vivo (Van Lear et al. 1973)
Sources:
Polyfibrospongia maynardi - Caribbean sponge
5,6-dibromo-N-methyltryptamine
Activity: Unknown psychoactivity. Brominated tryptamines show a high affinity for human serotonin receptors (Hu et al. 2002. )
Shows antibiotic activity against gram negative and gram positive bacteria in vitro but not in vivo (Van Lear et al. 1973)
Sources:
Polyfibrospongia maynardi - Caribbean sponge
5,6-dibromo-DMT
Soluble in ethanol, ethyl acetate.
Activity: Unknown psychoactivity. Brominated tryptamines show a high affinity for human serotonin receptors (Hu et al. 2002. )
5,6-diBr-DMT showed significant antidepressant activity in the Porsolt forced swim test in rodents and in the chick anxiety-depression continuum model. (Kochanowska et al. 2008 )
5,6-dibromo-N,N-dimethyltryptamine produced significant antidepressant-like activity in the forced swim test and in the tail suspension test. It did not induce hyperlocomotion indicating that nonspecific stimulant effects did not account for the observed antidepressant-like action. (Diers et al. 2008 )
Sources:
Smenospongia aurea contained 5,6-diBr-DMT (over 0.2% dry wt.) and 4 other alkaloids. (Kochanowska et al. 2008 )
Smenospongia cerebriformis contained 5,6-diBr-DMT as a minor alkaloid. (Kochanowska et al. 2008 )
Verongula gigantea had 5,6-diBr-DMT identified in one of five specimens analyzed via spectroscopic means. (Ciminiello P., et al. 2000)
Verongula rigida contained 5,6-diBr-DMT (0.35% dry wt.) (Kochanowska et al. 2008 )