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Pure cocaine, also known as 'free-base', is a highly illegal, highly addictive recreational stimulant which influences the central nervous system, providing euphoric and anesthetic effects on the body (National Institute on Drug Abuse, 2016). Its been identified as a tropane alkaloid (amine), identified by its central tropane ring system and nitrogen which acts as nucleophile due to the lone pair of electrons present which would suggest that it acts as a base and can react with acids (salts) to form compounds such as cocaine hydrochloride which is water soluble at 200g per 100ml (Siegrist & Wiegand, 2014). Compared to free-base cocaine which is minimally soluble in water at 0.17g per 100ml, hence why cocaine is usually taken as a salt. Additionally, cocaine contains several functional groups including:
A (non-polar) benzene ring, identified by its symmetrical planar shape and C-H bonds which have opposing dipoles that cancel out, giving it no dipole and making it non-polar. Two asymmetrical (polar) esters shown by the red double bonded oxygens and a (polar) tertiary amine shown by the blue nitrogen connected to the tropane ring. Due to the electronegativity difference of the N and C atoms, with nitrogen having the greater electronegativity, I'd expect this functional group to be polar.
In terms of the overall reactivity of cocaine, I'd predict that due to the resonance structure and limiting reactivity of the benzene, that this would inhibit the chemical reactivity of cocaine, however due to the nucleophilic nature of the amine, this could leave it open to electrophilic reactions.

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Cocaine has four stereocenters shown by the four SP3 chiral carbons (highlighted in yellow), labelled 'C1, C2, C3 and C5 (red)' which can yield up to 16 different stereoisomers. The four chiral centers can be identified by the four substituent atoms bonded to each one.  Based on the above picture, we can determine from the circled chiral carbon (blue), that there is a counter-clockwise or S-configuration, based on the priority of the atoms around it (shown above as 1, 2 and 3 in blue). However, research suggests that stable isomers must have C1 and C5 chiral carbons in opposing R/S configurations in order to be stable (Amara, Koslowski & Zaidi, 2021).

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I will analyze the three hydrogens bonded to the electronegative oxygen, seen at the bottom of the molecule highlighted in yellow. Due to the hydrogens being bonded to an electronegative oxygen, I'd expect them to be more chemically shifted than the three hydrogens bonded to the less electronegative nitrogen as seen at the top of the molecule. Furthermore, as there are no neighboring hydrogens, I'd expect the spectra to show a singlet with an integration of 3, due to the three hydrogens. This singlet can be seen sitting around 3.7 PPM compared to the singlet at 2.6 PPM, which represents the three hydrogens bonded to the nitrogen. Furthermore, the two hydrogens highlighted in green and identified as a multiplet due to their hydrogen neighbours and with an intergration of 2, are the most shifted which is expected due to their adjacent position to the electronegative oxygen within the local ester group.

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There are several ways cocaine and other illicit drugs impact the environment, one of the main impacts being large-scale deforestation which has heavily contributed to the loss of biodiversity and land degradation (Brombacher, D. et al, 2021). Countries such as Columbia which account for the highest production levels of Cocaine in the world, saw a 31% increase in cocaine production, accounting for 1400 tons, cultivated over 171,000 hectares (BBC, 2017). Whilst being detrimental to human and societal health, the production, plantation and harvest of cocaine has led to the toxification of our ecosystems, increased greenhouse gas emissions and contributed to unsustainable water usage particularly in areas in and around South America (Burns-Edel & Davis, 2016).

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Cocaine has many dire consequences on the environment ranging from largescale deforestation seen in several South American countries to increased concentrations of the drug being found in rivers and waterways which is having negative impacts on marine life. A 2019 article highlighted the impact cocaine has on marine life particularly in the river Thames in London and the direct impact on eels. It was found that roughly 4.4 pounds of cocaine entered the river Thames vis sewage systems on a daily basis. Due to this, research showed increased accumulation of the drug in the muscles, gills, brain and skin of eels with signs of increased hyperactivity in addition to high levels of damage to their muscular skeletal systems with no signs of healing  after 10 days (Martin, 2019).

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First reaction:
- Third tier amine (red), acts as a nucleophile due to the lone pair of electrons that can be easily donated during a reaction. This allows it to undergo electrophilic addition with an electrophile, hydrochloric acid (HCL). HCl donates a H+ proton to the nitrogen leaving the molecule ionized and water soluble (blue). This process turns the drug into a form of salt, increasing water solubility and allowing it to easily enter the bloodstream through nasal or blood passages.

Second reaction:
- Ecgonine Methyl Ester (EME) is one of the major cocaine metabolites and is often found in the plasma and urine of humans and other animals which indicates the consumption of cocaine (Pane, Traystman & Gleason, 1997). However, in recent years, scientist and engineers are looking at ways to hydrolyze cocaine with a catalyst such as cocaine esterase (CocE), a type of enzyme, to produce EME and benzoic acid which could be used as a means to treat cocaine addiction and overdoses (Berg, 2014). Hydrolysis is a type of nucleophilic substitution where water (H2O) which acts as a nucleophile, interacts with cocaine at the benzoyl ester pathway (red) producing EME and benzoic acid. Hydrogens are transferred from the water molecule tearing it apart and forming a carboxylic acid (blue) bonded to the benzene ring (benzoic acid) and alcohol (blue) on the EME molecule. In a natural context, cocaine within the body is broken down by enzymes and water (hydrolysis) into smaller molecules so our bodies have an easier time absorbing the compounds.