5-MeO-AMT

Systematic (IUPAC) name
1-(5-methoxy-1H-indol-3-yl)propan-2-amine
Clinical data
Pregnancy cat.	?
Legal status	not scheduled (US)
Routes	Oral
Identifiers
CAS number	1137-04-8 N
ATC code	?
PubChem	CID 36906
ChemSpider	33864 Y
ChEMBL	CHEMBL31115 Y
Chemical data
Formula	C12H16N2O
Mol. mass	204.2712 g/mol
SMILES O(c1cc2c(cc1)ncc2CC(N)C)C
InChI InChI=1S/C12H16N2O/c1-8(13)5-9-7-14-12-4-3-10(15-2)6-11(9)12/h3-4,6-8,14H,5,13H2,1-2H3 Y Key:OGNJZVNNKBZFRM-UHFFFAOYSA-N Y
Physical data
Melt. point	216–218 °C (421–424 °F)
N (what is this?)  (verify)

5-MeO-AMT or 5-methoxy-α-methyltryptamine, α,O-Dimethylserotonin (Alpha-O) is a potent psychedelic tryptamine. It is soluble in alcohol.

  Pharmacology

The sympathomimetic effects may in turn be caused by 5-MeO-AMT's structural similarity to the amphetamines. As noted by Alexander Shulgin, the alpha-methylated tryptamines can be looked at as the tryptamine homologues of the amphetamines (alpha-methylated phenethylamines).

Mechanisms of action such as inhibition of monoamine reuptake may be involved also.^[1]

  Recreational usage

  5-MeO-AMT blotters.

5-MeO-AMT is supposedly sold in 4 mg tablets by the street name Alpha-O and taken as a recreational drug. Since the DEA arrests of the makers of a huge percentage of the United States' LSD in 2000, 5-MeO-AMT may have occasionally been sold under the guise of LSD in liquid, sugar cube, or blotter form, though this may be due to DEA reports of finding it on sugar cubes and blotters "LSD Style".^[2][3]

The most common route of administration for 5-MeO-AMT is orally, however anecdotal reports have stated less common methods such as snorting or smoking. Intravenous (IV) and intramuscular (IM) routes are rarely, if ever, used outside research settings due to the high potency, powerful effects and quicker onset.

  Effects

  Tabs of gelatin containing 5-MeO-AMT.

The effects of 5-MeO-AMT occur at 4–7 mg orally for most users.

Erowid lists the following effects:^[4]

  Positive

• Increased energy
• Improved mood heading into euphoria at higher doses
• Increased sociability, gregariousness
• Increased giggling and laughing
• Increased sense of creative thinking
• Increased pleasure from sense of touch
• Intensification in sexual / erotic experiences for some users

  Neutral

• Light headedness
• Brightening of colors
• Visuals including motion, waves, breathing walls, etc. (usually at doses over 4–5 mg)
• Increased attention on details
• Auditory distortions or hallucinations (usually at higher doses)

  Negative

Expected at any dose:

• Headache
• Body fatigue
• Chills from slightly elevated body temperature (potential dehydration)
• Stress and extreme fatigue from long duration of effects.

At higher doses or pending potential allergic/histamine reaction:

• Nausea, diarrhea
• Vomiting at high doses

High dose side effects:

• Difficulty sleeping or resting for 12–24 hours after ingestion.
• Paranoia, irritability, anxiety (increasing with dose).
• Delusional, aggressive, or dissociated behaviour at very high doses (20+ mg)

  Dangers

If misrepresented as LSD, 5-MeO-AMT can be extremely dangerous; users may take a number of "hits" of 5-MeO-AMT, assuming that it is LSD. Unlike LSD, which is considerably safer in overdose, 5-MeO-AMT can be very harmful or fatal. Particularly sensitive individuals can experience symptoms of overdose at dosages in the normal (for most users) range — as low as 20 mg. This has led to at least a few hospitalizations and possibly more than one death.^[5] It is likely that the overdose potential of the compound is due to its sympathomimetic effects, as the side effects noted in overdose cases include cardiac arrhythmia and seizure. It also seems that oral consumption is safer than insufflation.^{[citation needed]}

Gloria Discerni, 18, died after overdosing on a drug initially believed to be LSD. Authorities learned months later that the drug wasn't LSD but a "designer drug" identified as 5-MeO-AMT.^{[citation needed]}

  Legality

According to the US Department of Justice, 5-MeO-AMT is illegal for human consumption. US DOJ claims it is an analog of 5-MeO-DiPT and alpha-methyltryptamine (AMT), which are Schedule I drugs under the Controlled Substances Act. According to the Federal Analog Act (21 U.S.C. § 813), "a controlled substance analog(ue) shall, to the extent intended for human consumption, be treated, for the purposes of any Federal law as a controlled substance in Schedule I." Thus, authorities can prosecute drug offenses involving 5-MeO-AMT in the same manner as offenses involving 5-MeO-DiPT and AMT. (See 21 U.S.C. § 802(32) for the definition of a controlled substance analog(ue).)^[6]

  See also

• 5-MeO-DMT
• 5-MeO-DPT
• 5-MeO-DiPT
• AMT

  References

  External links

• DEA forensic journal on 5-MeO-AMT
• Erowid 5-MeO-AMT vault
• Lycaeum 5-MeO-AMT page
• TiHKAL entry
• 5-MeO-AMT (α,O-DMS) entry in TiHKAL • info