Introduction to DOI

First discovered by Alexander Shulgin, DOI is a powerful psycedelic, acting as a partial agonist for the 5-HT2A, 5-HT2B, and 5-HT2C serotonin receptors with the hallucinogenic effects primarily being derived from the agonism of the 5-HT2A receptor. DOI has been shown to bind to the 5-HT2 receptors with Ki values of 0.7 nM for 5-HT2A, 20 nM for 5-HT2B, and 2.4 nM for 5-HT2C.

Aside from its psychoactive effects DOI has been shown to act as a powerful anti-inflammatory drug by inhibiting the tumor necrosis factor-alpha, an inflammatory mediator and target for several degenerative conditions which involve tissue damage through chronic inflammation such as arthritis and alzheimer's disease.

Using DOI

Ways of Administration

DOI is most commonly administered sublingually, buccally, or orally, often in the form of a liquid solution or on pre measured squares of blotter paper.

Effects of DOI

Positive

• Increased energy
• Abstract/creative though process
• Increased musical appreciation
• Mood lift
• Euphoria

Neutral

• Closed and open eye visual hallucinations
• Time distortion

Negative

• Anxiety
• Paranoia
• Possibility for a psychedelic crisis to unfold
• Body load

Chemistry of DOI

Column 1	Column 2
Systematic(IUPAC) name:	1-(4-iodo-2,5-dimethoxyphenyl)-propan-2-amine
Synonyms:	DOI
Molecular Formula:	C11H16INO2, C11H16INO2.HCl
Molar mass:	321.16 g/mol (freebase), 357.62 g/mol (hydrochloride) [1]
CAS Registry Number:	42203-78-1
Melting Point:	200.9 °C (hydrochloride)[2]
Boiling Point:	no data
Flash Point:	no data
Solubility:	no data
Additionnal data:	no data
Notes:	none

[1]

Reagent test results of 2C-C

The Dangers of DOI

There are several dangers which are involved with the administration of DOI on human beings...

• DOI is a research chemical, thus there is limited information on its effects and side effects due to a lack of formal trials on the compound.
• DOI takes a considerable amount of time to take effect, thus a user may be tempted to redose in turn putting themselves in a very dangerous situation.

These are the dangers common to all psychedelic drugs:

Accidental injury. When on a psychedelic drug, it is easier to accidentally injure yourself. Also because of the disorientating and potentially delusion inspiring nature of the experience, you could be lead to inflict harm on others or yourself. People have fallen off rooftops, run into traffic, attempted to throw people off rooftops as 'sacrifices', drowned, and so on. The best way of protecting against this is to have a friend with you who is sober to look after you and handle any negative situation that might arise.

Bad trips. A bad trip is a negative psychedelic experience. It can range from a mildly negative feeling of anxiety/discomfort, to full-blown psychosis. Bad trips usually ruin a psychedelic experience for the tripper and everyone else. Most bad trips are manageable, just very uncomfortable and difficult. Some are extreme and unmanageable though. It's not uncommon for a bad trip to result in lingering psychological issues. Usually just a few days of negative emotions and anxiety. Sometimes, however, a week or so of serious anxiety, destabilized mental state and impaired functioning is possible. On very rare occasions, a month or two of severely diminished functioning, traumatized mental state, depression & crippling anxiety can occur. More information on bad trips can be found here. The best way of avoiding a bad trip is having the correct set and setting.

Permanent psychosis. Psychedelics are believed by researchers not to cause permanent psychosis, however they could trigger a latent mental illness in someone who was already predisposed to it, or make existing mental illnesses worse. If there is a history of mental illness in your family, you are more likely to be predisposed. Everyone is at some risk, however.

PTSD, anxiety disorder, depression & depersonalization. There are anecdotal reports of the trauma inflicted by some bad trips leading to depression and anxiety which while usually temporary, could potentially develop into lasting disorders. While no different to the potential of any traumatic event to cause lasting disorders, nonetheless this is a danger of psychedelic drug use.

Legal Status of DOI

United Nations

USA

While DOI is not explicitly controlled within the United States, it be considered an analog of DOB thus falling under the Federal Analog Act.

DOI is considered to be a Schedule I substance in the state of Florida.

EU

Other Countries

Australia

DOI is a controlled substance in Australia.

Denmark

As of April 8, 2007 DOI is considered to be a Schedule I substance in the country of Denmark.

Japan

DOI is considered to be a designated substance under the Pharmaceutical Affairs Law making it illegal to buy, sell, posses, or consume in the country of Japan.

New Zealand

DOI is considered to be a Schedule III substance in the country of New Zealand under the "catch-all analogues" section of their drug laws.

Sweden

As of May 1, 2007 DOI is considered to be a controlled substance in the country of Sweden.

DOI

References

[1] Calculated from Atomic Weights of the Elements, 2007
[2] DOI monograph