2C-B

Discovery of 2C-B Synthesized in 1974 by Alexander

Shulgin Listed in Phenethylamines I Have Known

and Loved (PiHKAL) Psychedelic phenethylamine structurally

similar to mescaline/DOB Discovered while exploring homologues

of DOB

Discovery Bioassayed in man by Shulgin on June

25th 1975 “beautifully active” psychedelic

compound

Alexander Shulgin Research chemist at Dow Chemical

Invented first biodegradable pesticide (Zectran)

Developed new synthesis for MDMA Introduced it to Leo Zeff for use in

psychotherapy

Discovery Alexander Shulgin

Chemist who specialized in the creation of and experimentation with mind-altering substances

Created nearly 200 chemical compounds Stimulants Depressants Aphrodisiacs, ‘Empathogens’ Convulsants

Shulgin attended Harvard, and later earned his doctorate in biochemistry from the University of California, Berkeley

His interest in creating mind-altering substances began during his time serving in World War II

DEA consultant and drug analyst Possessed Schedule I DEA license DEA raided his lab in 1993 and revoked

license after PiHKAL published Continued to produce novel psychedelics

TiHKAL published in 1997 Died at 88 in June 2014

Synthesis of 2C-B Synthesized from 2,5-dimethoxybenzaldehyde Produced 2,5-dimethoxyphenethylamine

(2C-H) Brominated at the “magic” 4’ position

2,5-DMBA

2C-H

Chemical Composition 2C is an acronym for the 2 carbon

atoms between the benzene ring Substituted phenethylamine C10H14BrNO2

Popular usage Saw usage as an aid for

psychological/psychiatric therapy Popular for transient duration, light

nature, lack of side effects Became popular in the clubbing/rave

scene after MDMA placed into Schedule I on March 23, 1988

Legal Status Made schedule II drug in Convention on

Psychotropic Substances (UN International treaty) in 2001

US review on December 20, 1994 DEA makes SI on July 2, 1995

Many structural analogues sold after ban 2C-E, 2C-I, 2C-T-2, 2C-T-7 Illegal for human consumption under

Federal Analogue Act

Duration of action 4-8 hour duration (oral administration)

Onset 45-75 minutes Come up 15-30 minutes Plateau 2-4 hours Come down 1-2 hours After effects 2-4 hours

Duration (continued) Total 4-6 hour duration

2-4 hours insomnia/altered mindset after Little to no residual effects next day Relative lack of negative effects

Effects Positive:

Mood lift, euphoria, laughing, empathy, insight

Color/visual enhancement Open and closed eye visuals Mental and physical stimulation Tactile + erotic sensations Spiritual experiences/idea

Effects (Continued) Neutral: Change in consciousness,

anorexia, pupil dilation, restlessness Unusual thought/speech, time dilation Strange body sensations

Skin flushing, chills, energy surges Altered body temperature Ego softening

Effects (Continued) Negative: Sweating/chills, nausea,

vomiting, muscle twitching Confusion, lack of concentration, inability

to focus, insomnia, unwanted visions Unwanted/difficult experiences or feelings Paranoia, fear, panic

Subjective descriptions Mild psychedelic, less mind expanding

Less ego softening than psilocin/LSD OEV: crawling, shifting, cartoonish CEV: color shifts, patterning Large body load Stomach discomfort

Diarrhea, nausea, vomiting

Subjective descriptions Change in mucous production, coughing Positive mood push vs. other

psychedelics Mild stimulant effects Less forceful than MDMA

No MDMA aftereffects (crash/hangover) More psychedelic than MDMA No forced euphoria or experience

Subjective descriptions Erotic, sensual, aphrodisiac Altered linguistic skills More malleable than other psychedelics

Easier to control Allows introspection and work on

personal issues Analyze emotional issues

Cold, shivers, tremors during come up

Dosage Oral dosage

2-5mg threshold 15-25mg common 25-50mg strong Highly variable

Standard dose 10-40mg (Erowid Vault)

Addiction/dependence Not physically addiction

Unlikely to cause psychological addiction No reported withdrawal effects upon

cessation Strong transient tolerance

Need to double dose daily to get same effect

Tolerance lasts 5-7 days

Routes of Administration Oral Insufflation (Burning sensation, caustic,

highly painful) Rectal Vaporization Sublingual (caustic) Intramuscular (burning/caustic) Intravenous (burning/caustic)

Pharmacology Possible partial agonist or full antagonist

of 5-HT2A Receptors on apical dendrites of

pyramidal cells in prefrontal cortex 5-HT2C mostly responsible for effects

5-HT2A antagonism or activation in 5-HT2A-coupled phospholipase D pathway may contribute

Pharmacology (continued) Found to increase dopamine in rats Affinity for 5-HT3 causes nausea and

vomiting

Metabolism Deamination and demethylation in liver

Oxidative deamination 2-(4-bromo-2,5-dimethoxyphenyl)-ethanol

(BDMPE) 4-bromo-2,5-dimethoxyphenylacetic acid

(BDMPAA) 4-bromo-2,5-dimethoxybenzoic acid

(BDMBA)

Health Risks Use with MAOI may cause

hyperintensive crisis, highly dangerous Impaired driving/operation of machinery Seizure/convulsive disorder risk Elevated heart rate risk for those with

heart disease Diabetics should control blood sugar

Health Risks (Continued) Poor set and setting (environment and

mental state) may lead to psychological upheaval Can cause immensely difficult

experiences Trigger onset of predisposed mental

illness Schizophrenia

Anxiety, frightening thoughts/visuals Risk of HPPD as with all psychedelics

References Weber, B. (2014). Alexander Shulgin, psychdeleia

researcher, dies at 88. The New York Times. Web."Erowid 2C-B (2CB) Vault." Erowid 2C-B (2CB) Vault. N.p., n.d.

Web. 01 Apr. 2015."2C-B." NeuroSoup. N.p., 08 Apr. 2013. Web. 01 Apr. 2015."Shulgin, A (1991) ''PIHKAL''